Uracils having a herbicidal activity

ABSTRACT

New uracils are described, having general formula (I) and their use as herbicides.

CROSS-REFERENCE TO RELATED APPLICATIONS

Not Applicable

STATEMENT REGARDING FEDERALLY SPONSORED RESEARCH OR DEVELOPMENT

Not Applicable

INCORPORATION-BY-REFERENCE OF MATERIAL SUBMITTED ON A COMPACT DISK

Not Applicable

REFERENCE TO A MICROFICHE APPENDIX

Not Applicable

BACKGROUND OF THE INVENTION

1 Field of the Invention

The present invention relates to new uracils.

More specifically, the present invention relates to new uracils having ahigh herbicidal activity, the processes for their preparation andmethods for their use as herbicides for controlling weeds inagricultural crops.

2 Description of Related Art

Uracils having a herbicidal activity are described, among others, inpatents or patent applications U.S. Pat. No. 4,859,229, U.S. Pat. No.5,084,084, EP 1122244 and WO 01/77084.

BRIEF SUMMARY OF THE INVENTION

The Applicant has now surprisingly found uracils which, compared to theproducts described in the above patents or patent applications, showenhanced characteristics in terms of herbicidal activity with respect toweeds and/or in terms of a lower phytotoxicity for crops of agriculturalinterest.

DETAILED DESCRIPTION OF THE INVENTION

The object of the present invention therefore relates to new uracilshaving general formula (I):

wherein:

-   -   X₁ represents a hydrogen atom or a halogen atom;    -   X₂ represents a halogen atom;    -   X₄ represents a C₁-C₃ haloalkyl group;    -   R represents a hydrogen atom, a C₁-C₃ alkyl group or a C₁-C₃        haloalkyl group;    -   G represents an oxygen atom or a sulphur atom;    -   X₃ represents a Q(CR₁R₂)_(n)Z— group, a Q₁Z group, a Q₂- group,        a Y(OC)—CR₆═CR₅—CR₃R₄Z— group;    -   Z represents an oxygen atom or a sulphur atom;    -   R₁, R₂, R₃ and R₄, the same or different, represent a hydrogen        atom, a C₁-C₄ alkyl group or a C₁-C₄ haloalkyl group;    -   R₅ represents an OR₇ group;    -   R₆ represents a hydrogen atom or a C₁-C₄ alkyl group;    -   R₇ represents a C₁-C₄ alkyl group or a C₁-C₄ haloalkyl group;    -   Y represents an OR₈ group, a SR₉ group, a NR₁₀R₁₁ group;    -   R₈ and R₉ represent a hydrogen atom, a C₁-C₆ linear or branched        alkyl group, a C₁-C₆ linear or branched haloalkyl group, a C₃-C₆        cycloalkyl group, a C₄-C₉ cycloalkylalkyl group, a C₃-C₆        cyanoalkyl group, a C₃-C₆ alkoxyalkyl group, an oxethanyl group,        a tetrahydrofuranyl group; a phenyl group, a C₇-C₁₂ phenylalkyl        group, a pyridyl group, said groups, in turn, possibly        substituted with one or more halogen atoms selected from        chlorine, fluorine, bromine or iodine, or substituted with one        or more groups selected from C₁-C₄ alkyl, or C₁-C₄ haloalkyl,        C₁-C₄ alkoxy or C₁-C₄ haloalkoxy;    -   R₁₀ and R₁₁, the same or different, represent a hydrogen atom,        or a C₁-C₆ alkyl group, a C₁-C₆ haloalkyl group, a C₃-C₆        cycloalkyl group, a C₇-C₁₂ arylalkyl group, or an aryl group,        said groups, in turn, possibly substituted with one or more        halogen atoms selected from chlorine, fluorine, bromine or        iodine, or substituted with one or more groups selected from a        C₁-C₄ alkyl, or C₁-C₄ haloalkyl, C₁-C₄ alkoxy or C₁-C₄        haloalkoxy; or, jointly represent a C₂-C₇ alkylene chain        possibly substituted with C₁-C₄ alkyl groups and possibly        interrupted by oxygen atoms or by a NR₁₂ group, wherein:    -   R₁₂ represents a hydrogen atom, a C₁-C₆ alkyl group or C₁-C₆        haloalkyl group, a C₃-C₆ alkenyl group or a C₃-C₆ haloalkenyl        group, a C₃-C₆ alkynyl group or C₃-C₆ haloalkynyl group, a C₂-C₈        alkoxyalkyl group or a C₂-C₈ haloalkoxyalkyl group, a C₂-C₇        alkylcarbonyl group or C₂-C₇ haloalkylcarbonyl group:    -   n represents 1, 2 or 3;    -   Q represents a heterocyclic group selected from pyrrol-2-yl,        pyrrol-3-yl, imidazol-2-yl, imidazol-4-yl, imidazol-5-yl,        pyrazol-3-yl, pyrazol-4-yl, pyrazol-5-yl, 1,2,4-triazol-3-yl,        1,2,4-triazol-5-yl, 1,2,4-triazol-3-onyl, 1,2,3-triazolyl,        tetrazolyl, oxazolyl, isoxazol-5-yl, thiazol-2-yl, thiazol-5-yl,        isothiazolyl, 1,3,4-oxadiazolyl, 1,3,4-thiadiazolyl,        1,2,4-thiadiazolyl, 1,2,4-oxadiazolyl,        1,2,4-oxadiazol-5-on-3-yl, benzoxazol-2-yl, benzothiazol-2-yl,        pyrazinyl, pyridazinyl, 1,2,4-triazinyl,        1,3,4-thiadiazol-2-on-5-yl, 1,4,2-dioxazol-5-on-3-yl,        1,4,2-oxathiazol-5-on-3-yl, 1,3,4-oxadiazin-5-on-2-yl,        1,4,2-dioxazin-3-yl, 1,2,4-oxadiazin-5-on-3-yl, 4, 5, 6,        7-tetrahydro-1,3-benzothiazol-2-yl,        5,6-dihydro-4H-cyclopenta[d][1,3]thiazole, said groups, in turn,        possibly substituted with halogen atoms selected from chlorine,        fluorine, bromine or iodine, or substituted with groups selected        from C₁-C₆ alkyl or C₁-C₆ haloalkyl, C₂-C₆ alkenyl or C₂-C₆        halo-alkenyl, C₂-C₆ alkenyloxy or C₂-C₆ haloalkenyloxy, C₂-C₆        alkynyl or C₂-C₆ haloalkynyl, C₂-C₆ alkynyloxy or C₂-C₆        haloalkynyloxy, C₁-C₆ alkoxy or C₁-C₆ haloalkoxy, C₂-C₆        alkoxyalkyl or C₂-C₆ haloalkoxyalkyl, C₂-C₆ alkoxyalkoxy, C₂-C₆        haloalkoxyalkoxy, C₂-C₆ haloalkoxyhaloalkoxy, C₃-C₈        alkoxyalkoxyalkyl, C₃-C₈ alkoxyalkoxyalkoxy, C₁-C₆ alkylthio or        C₁-C₆ haloalkylthio, C₂-C₆ alkylthioalkyl, C₁-C₆ alkylsulfinic        or C₁-C₆ haloalkylsulfinic, C₁-C₆ alkylsulfonic or C₁-C₆        haloalkylsulfonic, C₂-C₆ alkoxycarbonyl or C₂-C₆        haloalkoxycarbonyl, C₃-C₇ alkenyloxycarbonyl or C₃-C₇        alkynyloxycarbonyl, C₃-C₈ alkoxycarbonylalkyl or C₃-C₈        haloalkoxycarbonylalkyl, C₄-C₉ alkenyloxycarbonylalkyl or C₄-C₉        alkynyloxycarbonylalkyl, C₃-C₇ alkoxycarbonylalkoxy, C₄-C₉        alkenyloxycarbonylalkoxy or C₄-C₉ alkynyloxycarbonylalkoxy,        C₃-C₈ aminocarbonylalkoxy possibly substituted with C₁-C₄ alkyl        groups or with a C₂-C₅ alkylene group; CN, CHO, NO₂, NH₂, OH,        C₁-C₃ cyanoalkyl, C₁-C₃ cyanoalkyloxy, C₂-C₆ formylalkyl, C₂-C₆        alkylcarbonyl, C₂-C₆ haloalkylcarbonyl, C₃-C₇        alkylcarbonylalkyl, C₂-C₆ alkoxyimino, C₂-C₆ haloalkoxyimino,        C₃-C₆ alkoxyiminoalkyl, C₃-C₆ haloalkoxyiminoalkyl, C₃-C₆        alkoxyiminohaloalkyl, aminocarbonyl, C₂-C₆ aminocarbonylalkyl,        aminosulfonyl or C₂-C₆ aminosulfonylalkyl, these last four        groups possibly substituted with one or two C₁-C₄ alkyl groups        or with a C₂-C₅ alkylene group; C₁-C₆ alkylsulfonylamino, C₂-C₇        alkylcarbonylamino or C₂-C₇ alkoxycarbonylamino, these last        three groups possibly substituted with C₁-C₄ alkyl groups;        C₆-C₁₀ aryl, C₆-C₁₂ arylalkyl, C₆-C₁₀ arylalkoxy, C₇-C₁₂        aryloxyalkyl, C₈-C₁₂ arylalkyloxyalkyl said groups in turn        possibly substituted with halogen atoms, C₁-C₄ alkyl groups,        C₁-C₃ haloalkyl groups, C₁-C₄ alkoxy groups, C₁-C₃ haloalkoxy        groups, CN; C₃-C₇ cycloalkyl, C₆-C₁₂ cycloalkylalkyl, C₆-C₁₀        cycloalkylalkoxy, tetrahydropyran-2-yl said groups in turn        possibly substituted with halogen atoms, C₁-C₄ alkyl groups,        C₁-C₄ alkoxy groups;    -   Q₁ represents a heterocyclic group selected from        1,3,4-thiadiazol-2-yl, 1,3,4-thiadiazol-5-yl,        1,2,4-thiadiazol-5-yl, tetrazol-5-yl, 1,3,4-oxadiazol-2-yl,        1,3,4-oxadiazol-5-yl, 1,2,4-oxadiazol-5-yl, oxazol-2-yl,        oxazol-4-yl, oxazol-5-yl, isoxazol-3-yl, isoxazol-5-yl,        thiazol-2-yl, thiazol-4-yl, thiazol-5-yl, said groups, in turn,        possibly substituted with halogen atoms selected from chlorine,        fluorine, bromine or iodine, or substituted with groups selected        from C₁-C₆ alkyl or C₁-C₆ haloalkyl, C₂-C₆ alkenyl or C₂-C₆        haloalkenyl, C₂-C₆ alkenyloxy or C₂-C₆ haloalkenyloxy, C₂-C₆        alkynyl or C₂-C₆ haloalkynyl, C₂-C₆ alkynyloxy or C₂-C₆        haloalkynyloxy, C₁-C₆ alkoxy or C₁-C₆ haloalkoxy, C₂-C₆        alkoxyalkyl or C₂-C₆ haloalkoxyalkyl, C₁-C₆ alkylthio or C₁-C₆        haloalkylthio, C₁-C₆ alkylsulfinic or C₁-C₆ haloalkylsulfinic,        C₁-C₆ alkylsulfonic or C₁-C₆ haloalkylsulfonic, C₂-C₆        alkoxycarbonyl or C₂-C₆ haloalkoxycarbonyl, C₃-C₈        alkoxycarbonylalkyl or C₃-C₈ haloalkoxycarbonylalkyl, C₃-C₈        alkoxycarbonylalkoxy, C₃-C₈ aminocarbonylalkoxy possibly        substituted with C₁-C₄ alkyl groups or with a C₂-C₆ alkylene;        CN, CHO, NO₂, NH₂, C₁-C₃ cyanoalkyl, C₁-C₃ cyanoalkyloxy, C₂-C₆        alkylcarbonyl, C₂-C₆ haloalkylcarbonyl, C₃-C₆ alkoxyiminoalkyl,        C₃-C₆ haloalkoxyiminoalkyl, aminocarbonyl, C₂-C₆        aminocarbonylalkyl, aminosulfonyl or C₂-C₆ aminosulfonylalkyl,        these last four groups possibly substituted with one or two        C₁-C₄ alkyl groups or with a C₂-C₅ alkylene; C₁-C₆        alkylsulfonylamino, C₂-C₇ alkylcarbonylamino or C₂-C₇        alkoxycarbonylamino, these last three groups possibly        substituted with C₁-C₄ alkyl groups; C₆-C₁₀ aryl, C₆-C₁₂        arylalkyl, C₆-C₁₀ arylalkoxy, C₇-C₁₂ aryloxyalkyl, C₈-C₁₂        arylalkyloxyalkyl said groups in turn possibly substituted with        halogen atoms, C₁-C₄ alkyl groups, C₁-C₃ haloalkyl groups, C₁-C₄        alkoxy groups, C₁-C₃ haloalkoxy groups, CN; C₃-C₇ cycloalkyl,        C₆-C₁₂ cycloalkylalkyl, C₆-C₁₀ cycloalkylalkoxy,        tetrahydropyran-2-yl said groups in turn possibly substituted        with halogen atoms, C₁-C₄ alkyl groups, C₁-C₄ alkoxy groups;    -   Q₂ represents a heterocyclic group selected from tetrazol-5-yl,        thiazol-2-yl, thiazol-4-yl, thiazol-5-yl, isothiazol-3-yl,        isothiazol-4-yl, isothiazol-5-yl, 1,2,3-triazolyl,        benzoxazol-2-yl, benzothiazol-2-yl, pyrimidin-2-yl,        1,2,4-triazinyl, 1,3,5-triazinyl, 1,3,4-thiadiazol-2-on-5-yl,        1,4,2-dioxazol-5-on-3-yl, 1,4,2-oxathiazol-5-on-3-yl,        1,3,4-oxadiazin-5-on-2-yl, 1,4,2-dioxazin-3-yl,        1,2,4-oxadiazin-5-on-3-yl,        4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl,        5,6-dihydro-4H-cyclopenta[d][1,3]thiazole, said groups in turn        possibly substituted with halogen atoms selected from chlorine,        fluorine, bromine or iodine, or substituted with groups selected        from C₁-C₆ alkyl or C₁-C₆ haloalkyl, C₂-C₆ alkenyl or C₂-C₆        haloalkenyl, C₂-C₆ alkenyloxy or C₂-C₆ haloalkenyloxy, C₂-C₆        alkynyl or C₂-C₆ haloalkynyl, C₂-C₆ alkynyloxy or C₂-C₆        haloalkynyloxy, C₁-C₆ alkoxy or C₁-C₆ haloalkoxy, C₂-C₆        alkoxyalkyl or C₂-C₆ haloalkoxyalkyl, C₂-C₆ alkoxyalkoxy, C₂-C₆        haloalkoxyalkoxy, C₂-C₆ haloalkoxyhaloalkoxy, C₃-C₈        alkoxyalkoxyalkyl, C₃-C₈ alkoxyalkoxyalkoxy, C₁-C₆ alkylthio or        C₁-C₆ haloalkylthio, C₂-C₆ alkylthioalkyl, C₁-C₆ alkylsulfinic        or C₁-C₆ haloalkylsulfinic, C₁-C₆ alkylsulfonic or C₁-C₆        haloalkylsulfonic, C₂-C₆ alkoxycarbonyl or C₂-C₆        haloalkoxycarbonyl, C₃-C₇ alkenyloxycarbonyl or C₃-C₇        alkynyloxycarbonyl, C₃-C₈ alkoxycarbonylalkyl or C₃-C₈        haloalkoxycarbonylalkyl, C₄-C₉ alkenyloxycarbonylalkyl or C₄-C₉        alkynyloxycarbonylalkyl, C₃-C₈ alkoxycarbonylalkoxy,        alkenyloxycarbonylalkoxy C₄-C₉ or alkynyloxycarbonylalkoxy        C₄-C₉, C₃-C₈ aminocarbonylalkoxy possibly substituted with C₁-C₄        alkyl or with a C₂-C₅ alkylene; CN, CHO, NO₂, NH₂, OH, C₁-C₃        cyanoalkyl, C₁-C₃ cyanoalkyloxy, C₂-C₆ formylalkyl, C₂-C₆        alkylcarbonyl, C₂-C₆ haloalkylcarbonyl, C₃-C₇        alkylcarbonylalkyl, C₂-C₆ alkoxyimino, C₂-C₆ haloalkoxyimino,        C₃-C₆ alkoxyiminoalkyl, C₃-C₆ haloalkoxyiminoalkyl,        alkoxyiminohaloalkyl C₃-C₆, aminocarbonyl, C₂-C₆        aminocarbonylalkyl, aminosulfonyl or C₂-C₆ aminosulfonylalkyl,        these last four groups possibly substituted with one or two        C₁-C₄ alkyl groups or with a C₂-C₅ alkylene; C₁-C₆        alkylsulfonylamino, C₂-C₇ alkylcarbonylamino o C₂-C₇        alkoxycarbonylamino, these last three groups possibly        substituted with C₁-C₄ alkyl groups; C₆-C₁₀ aryl, C₆-C₁₂        arylalkyl, C₆-C₁₀ arylalkoxy, C₇-C₁₂ aryloxyalkyl, C₈-C₁₂        arylalkyloxyalkyl said groups in turn possibly substituted with        halogen atoms, C₁-C₄ alkyl groups, C₁-C₃ haloalkyl groups, C₁-C₄        alkoxy groups, C₁-C₃ haloalkoxy groups, CN; C₃-C₇ cycloalkyl,        C₆-C₁₂ cycloalkylalkyl, C₆-C₁₀ cycloalkylalkoxy,        tetrahydropyran-2-yl said groups in turn possibly substituted        with halogen atoms, C₁-C₄ alkyl groups, C₁-C₄ alkoxy groups.

A further object of the present invention relates to the use of uracilshaving general formula (I), as herbicides.

Specific examples of compounds having general formula (I) which areinteresting for their high herbicidal activity are:

-   methyl    (2E)-4-{2-chloro-4-fluoro-5-[1,2,3,6-tetrahydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenoxy}-3-methoxybut-2-enoate;-   methyl    (2E)-4-{2,4-dichloro-5-[1,2,3,6-tetrahydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenoxy}-3-methoxybut-2-enoate;-   methyl    (2E)-4-{2-chloro-4-fluoro-5-[1,2,3,6-tetrahydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenylthio}-3-methoxybut-2-enoate;-   ethyl    (2E)-4-{2-chloro-4-fluoro-5-[1,2,3,6-tetrahydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenoxy}-3-ethoxybut-2-enoate;-   methyl    (2E)-4-{2,4-dichloro-5-[1,2,3,6-tetrahydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenylthio}-3-methoxybut-2-enoate;-   ethyl (2E)-4-{2,4-dichloro-5-[1, 2, 3,    6-tetrahydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenoxy}-3-ethoxybut-2-enoate;-   isopropyl    (2E)-4-{2-chloro-4-fluoro-5-[1,2,3,6-tetrahydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenoxy}-3-methoxybut-2-enoate;-   methyl    (2E)-4-{2-chloro-4-fluoro-5-[1,2,3,6-tetrahydro-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenoxy}-3-methoxybut-2-enoate;-   methyl    (2E)-4-{2,4-dichloro-5-[1,2,3,6-tetrahydro-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenoxy}-3-methoxybut-2-enoate;-   ethyl    (2E)-4-{2-chloro-4-fluoro-5-[1,2,3,6-tetrahydro-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenoxy}-3-ethoxybut-2-enoate;-   ethyl    (2E)-4-{2,4-dichloro-5-[1,2,3,6-tetrahydro-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenoxy}-3-ethoxybut-2-enoate;-   2,2,2-trifluoroethyl    (2E)-4-{2-chloro-4-fluoro-5-[1,2,3,6-tetrahydro-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenoxy}-3-methoxybut-2-enoate;-   enoate;-   (2E)-4-{2-chloro-4-fluoro-5-[1,2,3,6-tetrahydro-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenoxy}-3-methoxy-N,N-dimethylbut-2-enamide;-   S-ethyl    (2E)-4-{2-chloro-4-fluoro-5-[1,2,3,6-tetrahydro-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenoxy}-3-methoxybut-2-enethioate;-   isopropyl    (2E)-4-{2,4-dichloro-5-[1,2,3,6-tetrahydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenoxy}-3-methoxybut-2-enoate;-   2,2,2-trifluoroethyl    (2E)-4-{2-chloro-4-fluoro-5-[1,2,3,6-tetrahydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenoxy}-3-methoxybut-2-enoate;-   2,2,2-trifluoroethyl    (2E)-4-{2,4-dichloro-5-[1,2,3,6-tetrahydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)    pyrimidin-1-yl]phenoxy}-3-methoxybut-2-enoate;-   S-ethyl    (2E)-4-{2-chloro-4-fluoro-5-[1,2,3,6-tetrahydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)    pyrimidin-1-yl]phenoxy}-3-methoxybut-2-enethioate;-   S-ethyl    (2E)-4-{2,4-dichloro-5-[1,2,3,6-tetrahydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenoxy}-3-methoxybut-2-enethioate;-   (2E)-4-{2-chloro-4-fluoro-5-[1,2,3,6-tetrahydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenoxy}-3-methoxy-N,N-dimethylbut-2-enamide;-   (2E)-4-{2,4-dichloro-5-[1,2,3,6-tetrahydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenoxy}-3-methoxy-N,N-dimethylbut-2-enamide;-   (2E)-4-{2-chloro-4-fluoro-5-[1,2,3,6-tetrahydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenylthio}-3-methoxy-N,N-dimethylbut-2-enamide;-   (2E)-4-{2,4-dichloro-5-[1,2,3,6-tetrahydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenylthio}-3-methoxy-N,N-dimethylbut-2-enamide;-   3-[4-chloro-2-fluoro-5-(tetrazol-5-ylmethoxy)phenyl]-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;-   3-{4-chloro-2-fluoro-5-[(2-methyl-2H-tetrazol-5-yl)methoxy]phenyl}-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;-   3-[4-chloro-2-fluoro-5-(tetrazol-5-ylmethoxy)phenyl]-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;-   3-[2,4-dichloro-5-(tetrazol-5-ylmethoxy)phenyl]-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;-   3-{4-chloro-2-fluoro-5-[(2-methyl-2H-tetrazol-5-yl)methoxy]phenyl}-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;-   3-{4-chloro-2-fluoro-5-[(2-ethyl-2H-tetrazol-5-yl)methoxy]phenyl}-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;-   3-{2,4-dichloro-5-[(2-methyl-2H-tetrazol-5-yl)methoxy]phenyl}-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;-   3-{2,4-dichloro-5-[(2-ethyl-2H-tetrazol-5-yl)methoxy]phenyl}-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;-   3-{4-chloro-2-fluoro-5-[(1-ethyl-1H-tetrazol-5-yl)methoxy]phenyl}-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;-   3-{2,4-dichloro-5-[(1-ethyl-1H-tetrazol-5-yl)methoxy]phenyl}-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;-   3-{5-[(5-tert-butyl-1,3,4-oxadiazol-2-yl)methoxy]-4-chloro-2-fluorophenyl}-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;-   methyl    [5-({2-chloro-4-fluoro-5-[1,2,3,6-tetrahydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenoxy}methyl)-1H-tetrazol-1-yl]acetate;-   methyl    [5-({2,4-dichloro-5-[1,2,3,6-tetrahydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenoxy}methyl)-1H-tetrazol-1-yl]acetate;-   methyl    [5-({2-chloro-4-fluoro-5-[1,2,3,6-tetrahydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenoxy}methyl)-2H-tetrazol-2-yl]acetate;-   methyl    [5-({2,4-dichloro-5-[1,2,3,6-tetrahydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenoxy}methyl)-2H-tetrazol-2-yl]acetate;-   3-[4-chloro-3-(tetrazol-5-yl)phenyl]-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;-   3-[4-chloro-3-(2-methyl-2H-tetrazol-5-yl)phenyl]-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;-   3-[4-chloro-3-(1-methyl-1H-tetrazol-5-yl)phenyl]-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;-   3-[4-chloro-3-(tetrazol-5-yl)phenyl]-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;-   3-[4-chloro-2-fluoro-5-(tetrazol-5-yl)phenyl]-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;-   3-[2,4-dichloro-5-(tetrazol-5-yl)phenyl]-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;-   3-[4-chloro-2-fluoro-5-(tetrazol-5-yl)phenyl]-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;-   3-[2,4-dichloro-5-(tetrazol-5-yl)phenyl]-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;-   3-[4-chloro-3-(2-methyl-2H-tetrazol-5-yl)phenyl]-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;-   3-[4-chloro-2-fluoro-5-(2-methyl-2H-tetrazol-5-yl)phenyl]-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;-   3-[2,4-dichloro-5-(2-methyl-2H-tetrazol-5-yl)phenyl]-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;-   3-[4-chloro-2-fluoro-5-(1-methyl-1H-tetrazol-5-yl)phenyl]-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;-   3-[2,4-dichloro-5-(1-methyl-1H-tetrazol-5-yl)phenyl]-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;-   3-[4-chloro-2-fluoro-5-(2-methyl-2H-tetrazol-5-yl)phenyl]-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;-   3-[2,4-dichloro-5-(2-methyl-2H-tetrazol-5-yl)phenyl]-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;-   3-[4-chloro-3-(2-ethyl-2H-tetrazol-5-yl)phenyl]-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;-   3-[4-chloro-3-(1-methyl-1H-tetrazol-5-yl)phenyl]-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;-   3-[4-chloro-2-fluoro-5-(1-methyl-1H-tetrazol-5-yl)phenyl]-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;-   3-[(2,4-dichloro-5-(1-methyl-1H-tetrazol-5-yl)phenyl]-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;-   3-[(4-chloro-3-(1-ethyl-1H-tetrazol-5-yl)phenyl]-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;-   methyl    (5-{2-chloro-5-[1,2,3,6-tetrahydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenyl}-1H-tetrazol-1-yl)acetate;-   methyl    (5-{2-chloro-5-[1,2,3,6-tetrahydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenyl}-2H-tetrazol-2-yl)acetate;-   methyl    (5-{2-chloro-4-fluoro-5-[1,2,3,6-tetrahydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenyl}-1H-tetrazol-1-yl)acetate;-   methyl    (5-{2-chloro-4-fluoro-5-[1,2,3,6-tetrahydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenyl}-2H-tetrazol-2-yl)acetate;-   methyl    (5-{2,4-dichloro-5-[1,2,3,6-tetrahydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenyl}-1H-tetrazol-1-yl)acetate;-   methyl    (5-{2,4-dichloro-5-[1,2,3,6-tetrahydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenyl}-2H-tetrazol-2-yl)acetate;-   3-[4-chloro-3-(4-methoxy-5-methyl-1,3-thiazol-2-yl)phenyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;-   3-[2,4-dichloro-5-(4-methoxy-5-methyl-1,3-thiazol-2-yl)phenyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;-   3-[4-chloro-2-fluoro-5-(4-methoxy-5-methyl-1,3-thiazol-2-yl)phenyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;-   3-[4-chloro-3-(4-methoxy-5-methyl-1,3-thiazol-2-yl)phenyl-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;-   3-[4-chloro-3-(4-ethoxy-5-methyl-1,3-thiazol-2-yl)phenyl-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-    pyrimidinedione;-   3-[(2,4-dichloro-5-(4-methoxy-5-methyl-1,3-thiazol-2-yl)phenyl-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;-   3-[2,4-dichloro-5-(4-ethoxy-5-methyl-1,3-thiazol-2-yl)phenyl-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;-   3-[4-chloro-2-fluoro-5-(4-methoxy-5-methyl-1,3-thiazol-2-yl)phenyl-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;-   3-[4-chloro-2-fluoro-5-(4-ethoxy-5-methyl-1,3-thiazol-2-yl)phenyl-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;-   3-[4-chloro-3-(4-benzyloxy-5-methyl-1,3-thiazol-2-yl)phenyl-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;-   3-[2,4-dichloro-5-(4-benzyloxy-5-methyl-1,3-thiazol-2-yl)phenyl-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;-   3-[4-chloro-2-fluoro-5-(4-benzyloxy-5-methyl-1,3-thiazol-2-yl)phenyl-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;-   3-(2,4-dichloro-5-{[5-(trifluoromethyl)-1,3,4-thiadiazol-2-yl]oxy}phenyl)-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;-   3-(4-chloro-2-fluoro-5-{[5-(trifluoromethyl)-1,3,4-thiadiazol-2-yl]oxy}phenyl)-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;-   3-(2,4-dichloro-5-{[5-(trifluoromethyl)-1,3,4-oxadiazol-2-yl]oxy}phenyl)-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;-   3-(4-chloro-2-fluoro-5-{[5-(trifluoromethyl)-1,3,4-oxadiazol-2-yl]oxy}phenyl)-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;-   3-(4-chloro-3-{[5-(trifluoromethyl)-1,3,4-thiadiazol-2-yl]oxy}phenyl)-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;-   3-(2,4-dichloro-5-{[5-(trifluoromethyl)-1,3,4-thiadiazol-2-yl]oxy}phenyl)-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;-   3-(4-chloro-2-fluoro-5-{[5-(trifluoromethyl)-1,3,4-thiadiazol-2-yl]oxy}phenyl)-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;-   3-{4-chloro-3-[(5-methyl-1,3,4-thiadiazol-2-yl)oxy]phenyl}-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;-   3-{2,4-dichloro-5-[(5-methyl-1,3,4-thiadiazol-2-yl)oxy]phenyl}-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;-   3-{4-chloro-2-fluoro-5-[(5-methyl-1,3,4-thiadiazol-2-yl)oxy]phenyl}-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;-   3-(4-chloro-3-{[5-(trifluoromethyl)-1,3,4-oxadiazol-2-yl]oxy}phenyl)-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;-   3-(2,4-dichloro-5-{[5-(trifluoromethyl)-1,3,4-oxadiazol-2-yl]oxy}phenyl)-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;-   3-(4-chloro-2-fluoro-5-{[5-(trifluoromethyl)-1,3,4-oxadiazol-2-yl]oxy}phenyl)-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;-   3-{4-chloro-3-[(5-methyl-1,3,4-oxadiazol-2-yl)oxy]phenyl}-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;-   3-{2,4-dichloro-5-[(5-methyl-1,3,4-oxadiazol-2-yl)oxy]phenyl}-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;-   3-{4-chloro-2-fluoro-5-[(5-methyl-1,3,4-oxadiazol-2-yl)oxy]phenyl}-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;-   methyl    (2E)-4-{2-chloro-4-fluoro-5-[1,2,3,6-tetrahydro-3-methyl-6-oxo-2-thioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenoxy}-3-methoxybut-2-enoate;-   methyl    (2E)-4-{2-chloro-4-fluoro-5-[1,2,3,6-tetrahydro-3-difluoromethyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenoxy}-3-methoxybut-2-enoate.

A further object of the present invention relates to processes for thepreparation of the compounds having general formula (I).

In particular, the compounds having general formula (I) can be preparedby the reaction of an isocyanate or isothiocyanate having generalformula (II) by cyclocondensation with a 3-aminocrotonate having generalformula (III) according to the reaction scheme 1.

In the general formulae indicated in this reaction scheme:

-   -   X₁, X₂, X₃, X₄, R and G have the meanings defined above;    -   R₁₃ represents a C₁-C₄ alkyl or C₁-C₄ haloalkyl group or a        phenyl group possibly substituted with C₁-C₄ alkyl groups.

The reaction between the compounds having general formula (II) and thecompounds having general formula (III) is preferably carried out in thepresence of an inert organic solvent and in the presence of an organicbase or preferably inorganic, at a temperature ranging from −20° C. tothe boiling point of the reaction mixture.

Examples of solvents which can be used for the above reaction includealiphatic or cyclo-aliphatic hydrocarbons (petroleum ether, hexane,cyclohexane, etc.), chlorinated hydrocarbons (methylene chloride,chloroform, carbon tetrachloride, dichloroethane etc.), aromatichydrocarbons (benzene, toluene, xylene, chlorobenzene, etc.), ethers(diethyl ether, diisopropyl ether, dimethoxy ethane, dioxane,tetrahydrofuran, etc.), alcohols and glycols (methanol, ethanol, methylcellosolve, ethylene glycol, etc.), ketones (acetone, methyl ethylketone, methyl propyl ketone, methyl isobutyl ketone etc.), nitriles(acetonitrile, benzonitrile, etc.), aprotic dipolar solvents(dimethylformamide, dimethylacetamide, hexamethylphosphoramide,dimethylsulfoxide, sulfolane, N-methylpyrrolidone, etc.).

Inorganic bases which can be used are, for example, hydrides, hydroxidesand carbonates of sodium and potassium.

Organic bases useful for the purpose are, for example, triethylamine,pyridine, 4-N,N-dimethylaminopyridine, N,N-dimethylaniline,N-methylpiperidine, lutidine, diazabicyclooctane (DABCO),diazabicyclononene (DBN), diazabicycloundecene (DBU).

Isocyanates or isothiocyanates having general formula (II) can beprepared starting from a suitable substituted aniline having generalformula (IV) by reaction with a compound having general formula (V),such as phosgene, diphosgene, triphosgene or thiophosgene, according tothe reaction scheme 2.

In the general formulae indicated in this reaction scheme:

-   -   X₁, X₂, X₃ and G have the meanings defined above;    -   L₃ and L₄, the same or different, represent a chlorine atom or a        CCl₃O— group.

The reaction is preferably carried out in the presence of an inertorganic solvent, at a temperature ranging from 0° C. to the boilingpoint of the mixture, possibly in the presence of a catalyst such astriethylamine, in an amount ranging from 0.001 to 100% by weight withrespect to aniline (IV).

Inert organic solvents useful for the purpose are, for example,chlorinated hydrocarbons (for example methylene chloride, chloroform,1,2-dichloroethane, etc.), aromatic hydrocarbons (for example, benzene,toluene, xylene, chlorobenzene, etc.), esters (for example ethylacetate, etc.). An amount of reagent (V) ranging from 1 to 3 moles permole of aniline (IV) is used in the reaction.

The compounds having general formula (I), wherein X₃ represents aQ(CR₁R₂)_(n)Z— group, a Q₁Z— group, a Y(OC)—CR₆═CR₅—CR₃R₄Z— group,compounds (Ia), can also be prepared by the reaction of a uracil havinggeneral formula (VI) with a compound having general formula (VII)according to the reaction scheme 3:

In the general formulae indicated in this reaction scheme:

-   -   X₁, X₂, X₄, G and Z have the meanings defined above;    -   R represents a C₁-C₃ alkyl group or a C₁-C₃ haloalkyl group;    -   W represents a Q(CR₁R₂)_(n)— group, a Q₁- group, a        Y(OC)—CR₆═CR₅—CR₃R₄— group, wherein R₁, R₂, R₃, R₄, R₅, R₆, Y, Q        and Q₁ have the meanings defined above;    -   L₂ represents a halogen atom, a R_(L)SO₂O— group, wherein R_(L)        represents a C₁-C₄ alkyl or C₁-C₄ haloalkyl group or a phenyl        group possibly substituted by C₁-C₄ alkyl groups, or it        represents a R_(L1)SO₂— group wherein R_(L1) represents a C₁-C₄        alkyl or C₁-C₄ haloalkyl group.

The reaction between the compounds having general formula (VI) and thecompounds having general formula (VII) is preferably carried out in thepresence of one or more inert organic solvents and in the presence of abase, preferably an inorganic base, at a temperature ranging from −10°C. to the boiling temperature of the reaction mixture.

Organic solvents useful for the purpose are, for example, aromatichydrocarbons (benzene, toluene, xylene, chlorobenzene, etc.), ethers(diethyl ether, diisopropyl ether, dimethoxyethane, dioxane,tetrahydrofuran, etc.), alcohols and glycols (methanol, ethanol, methylcellosolve, ethylene glycol, etc.), ketones (acetone, methyl ethylketone, methyl propyl ketone, methyl isobutyl ketone, etc.), nitrites(acetonitrile, benzonitrile, etc.), aprotic dipolar solvents(dimethylformamide, dimethylacetamide, hexamethylphosphoramide,dimethylsulfoxide, sulfolane, N-methylpyrrolidone, etc.).

Inorganic bases useful for the purpose are, for example, hydrides,hydroxides and carbonates of sodium or potassium.

The reaction can also be advantageously carried out in a biphasic systemusing, as the solvent, water and an organic solvent immiscible withwater, in the presence of phase transfer catalysts, according to what isdescribed by Dehmlow and Dehmlow in “Phase Transfer Catalysis” (1983),Verlag Chemie.

The compounds having general formula (I) wherein G=O and R≠H, compounds(Ic), can also be prepared by the reaction of a uracil having generalformula (Ib) with an alkylation compound having general formula (VIII)according to the reaction scheme 4.

In the general formulae indicated in this reaction scheme:

-   -   X₁, X₂, X₃ and X₄ have the meanings defined above;    -   R′ represents a C₁-C₃ alkyl or C₁-C₃ haloalkyl group;    -   L₁ represents a halogen atom, or a R_(L)SO₂O— group wherein        R_(L) represents a C₁-C₄ alkyl or C₁-C₄ haloalkyl group or a        phenyl group possibly substituted by C₁-C₄ alkyl groups.

The reaction between the compounds having general formula (Ib) and thecompounds having general formula (VIII) is preferably carried out in thepresence of one or more inert organic solvents and in the presence of abase, preferably an inorganic base, at a temperature ranging from −10°C. to the boiling temperature of the reaction mixture.

Organic solvents useful for the purpose are, for example, aromatichydrocarbons (benzene, toluene, xylene, chlorobenzene, etc.), ethers(diethyl ether, diisopropyl ether, dimethoxyethane, dioxane,tetrahydrofuran, etc.), alcohols and glycols (methanol, ethanol, methylcellosolve, ethylene glycol, etc.), ketones (acetone, methyl ethylketone, methyl propyl ketone, methyl isobutyl ketone, etc.), nitriles(acetonitrile, benzonitrile, etc.), aprotic dipolar solvents(dimethylformamide, dimethylacetamide hexamethylphosphoramide,dimethylsulfoxide, sulfolane, N-methylpyrrolidone, etc.).

Inorganic bases useful for the purpose are, for example, hydrides,hydroxides and carbonates of sodium and potassium.

The reaction can also be advantageously carried out in a biphasic systemusing, as solvent, water and an organic solvent immiscible with water,in the presence of phase transfer catalysts, according to what isdescribed by Dehmlow and Dehmlow in “Phase Transfer Catalysis” (1983),Verlag Chemie.

The compounds having general formula (I) wherein G=O, compounds (Id),can also be prepared starting from a suitably substituted aniline havingformula (IV) by reaction with a chloroformiate or a carbonate havingformula (IX) to give a carbamate having formula (X); this can beconverted to the compounds of general formula (Id) by cyclo condensationwith a 3-aminocrotonate having general formula (III).

This reaction sequence is shown in scheme 5.

In the general formulae shown in the reaction scheme:

-   -   X₁, X₂, X₃, X₄ and R have the meanings defined above;    -   L₅ represents a halogen atom or a OR₁₄ group;    -   R₁₃ and R₁₄ represent a C₁-C₄ alkyl or C₁-C₄ haloalkyl group or        a phenyl group possibly substituted by C₁-C₄ alkyl groups.

The reaction between aniline having general formula (IV) and a compoundhaving general formula (IX) is preferably carried out in the presence ofan inert organic solvent, at a temperature ranging from −10° C. to theboiling point of the mixture itself, in the presence of an organic orinorganic base, in an amount ranging from 1 to 1.5 moles per mole ofaniline (IV).

Inorganic bases useful for the purpose are, for example, sodiumcarbonate, sodium hydroxide, etc.

Organic bases useful for the purpose are, for example, triethylamine,pyridine, 4-dimethylaminopyridine, etc.

Inert organic solvents useful for the purpose are, for example,chlorinated hydrocarbons (for example, methylene chloride, chloroform,1,2-dichloroethane etc.), aromatic hydrocarbons (for example benzene,toluene, xylene, chlorobenzene, etc.), ethers (for example, ethyl ether,tetrahydrofuran, dioxane, etc.), esters (for example ethyl acetate,etc.).

A quantity of the compound having formula (IX) ranging from 1 to 1.5moles per mole of aniline (IV), is used in the reaction.

The operative conditions, as well as the typology of solvent and basesuseful for carrying out the cyclocondensation reaction of a carbamatehaving general formula (X) with a 3-aminocrotonate having generalformula (III) shown in scheme 5, are analogous to those shown for thereaction of scheme 1.

The compounds having general formula (I) wherein X₃=Q₂ can also beprepared starting from compounds having general formula (XI)

wherein:

-   -   X₁, X₂, X₄, R and G have the meanings defined above;    -   U represents a functional group which can be transformed into        one of the heterocyclic rings envisaged for Q₂.

For example, when U=CN, CONH₂, CSNH₂, CO₂H ecc., said functional groupscan be easily transformed into heterocyclic groups according to knowntechniques in organic chemistry.

Specific examples of this strategy, for example starting from the cyanofunctional group (U=CN), relate to the preparation of tetrazoles andthiazoles.

The cyano group can be transformed into a tetrazole, for example byreaction under heat with trimethyl silylazide, in toluene, catalysed bydibutyltin oxide, according to what is described in “Journal OrganicChemistry” (1993), vol. 58, pages 4139-4141, or by heating with sodiumazide in water and catalysis of ZnBr₂, as described in “Journal OrganicChemistry” (2001), vol. 66, pages 7945-7950.

The cyano group can be transformed into thiazole, for example byreaction under heat with α-mercapto acetic acids according to what isdescribed in “Journal Medicinal Chemistry” (1991), vol. 34, pages2158-2165, or by treatment with α-mercapto ketones and gaseoushydrochloric acid, in benzene, at 0° C., as described in C.A., 1958,vol. 52, 14698.

The compounds having general formula (Ib) can also be prepared startingfrom a suitable substituted aniline having general formula (IV) byreaction with a β-ketoester having general formula (XII), to give ananilide having general formula (XIII); this can be easily converted intothe intermediate of general formula (XIV) by amination with ammonia orammonium salts; this last intermediate can be converted into thecompounds of general formula (Ib) by cyclization with a compound ofgeneral formula (XV), such as phosgene, or diphosgene.

This reaction sequence is shown in scheme 6.

In the general formulae indicated in this reaction scheme:

-   -   X₁, X₂, X₃ and X₄ have the meanings defined above;    -   R₁₃ represents a C₁-C₄ alkyl or haloalkyl group or a phenyl        group possibly substituted by C₁-C₄ alkyl groups;    -   L₆ and L₇, having the same or different meaning, represent a        chlorine atom, a CCl₃O— group, a C₁-C₄ alkoxy group, a phenoxy        group, an imidazol-1-yl group or a 1,2,4-triazol-1-yl group.

The reaction between the compounds having general formula (IV) and thecompounds having general formula (XII) is preferably carried out in thepresence of one or more inert organic solvents, at a temperature rangingfrom −10° C. to the boiling temperature of the reaction mixture; anamount of compound (XII) ranging from 1 to 3 moles per mole of aniline(IV) is used in the reaction.

The reaction may also be carried out while distilling off compound R₁₃OHformed during the reaction, alone or in mixture with the solvent used.

Inert organic solvents useful for the purpose are, for example,aliphatic or cyclo-aliphatic hydrocarbons (petroleum ether, hexane,cyclohexane, etc.), chlorinated hydrocarbons (for example methylenechloride, chloroform, 1,2-dichloroethane, etc.), aromatic hydrocarbons(for example, benzene, toluene, xylene, chlorobenzene, etc.), ethers(for example diethyl ether, tetrahydrofuran, dioxane, etc.), nitriles(acetonitrile, benzonitrile, etc.), aprotic dipolar solvents(dimethylformamide, dimethylacetamide, hexamethylphosphoramide,dimethylsulfoxide, sulfolane, N-methylpyrrolidone, etc.).

The reaction may also be carried out in presence of a suitable organicbase, for example pyridine, 4-dimethylaminopyridine, etc., in an amountranging from 0.001 to 1 mole per mole of compound (IV).

The transformation of compounds having general formula (XIII) intocompounds having general formula (XIV) is preferably carried out in thepresence of one or more inert organic solvents, at a temperature rangingfrom −10° C. to the boiling temperature of the reaction mixture; in thereaction ammonia or a suitable ammonium salt, for example ammoniumacetate, is used in an amount ranging from 1 to 20 moles per mole ofcompound (XIII).

Inert organic solvents useful for the purpose are, for example,chlorinated hydrocarbons (for example methylene chloride, chloroform,1,2-dichloroethane, etc.), aromatic hydrocarbons (for example, benzene,toluene, xylene, chlorobenzene, etc.), ethers (for example diethylether, tetrahydrofuran, dioxane, etc.), nitriles (acetonitrile,benzonitrile, etc.), aprotic dipolar solvents (dimethylformamide,dimethylacetamide, hexamethylphosphoramide, dimethylsulfoxide,sulfolane, N-methylpyr-methylpyrrolidone, etc.).

Alternatively, when an ammonium salt is used, the reaction may becarried out in absence of solvent, at a temperature ranging from 20° C.to 200° C.

The reaction between the compounds having general formula (XIV) and thecompounds having general formula (XV) is preferably carried out in thepresence of one or more inert organic solvents, at a temperature rangingfrom −10° C. to the boiling temperature of the reaction mixture; anamount of compound (XV) ranging from 1 to 5 moles per mole of compound(XIV) is used in the reaction.

The reaction is preferably carried out in the presence of a suitableorganic or inorganic base, in an amount ranging from 1 to 5 moles permole of compound (XIV).

Inorganic bases useful for the purpose are, for example, hydroxides andcarbonates of sodium and potassium, etc.

Organic bases useful for the purpose are, for example, triethylamine,pyridine, 4-dimethylaminopyridine, etc.

In addition to the base a suitable catalyst is preferably used, forexample 4-dimethylaminopyridine, in an amount ranging from 0.001 to 1mole per mole of compound (XIV).

Inert organic solvents useful for the purpose are, for example, esters(for example ethyl acetate, etc.), chlorinated hydrocarbons (for examplemethylene chloride, chloroform, 1,2-dichloroethane, etc.), aromatichydrocarbons (for example, benzene, toluene, xylene, chlorobenzene,etc.), alcohols and glycols (methanol, ethanol, methyl cellosolve,ethylene glycol, etc.), ketones (acetone, methyl ethyl ketone, methylpropyl ketone, methyl isobutyl ketone, etc.), ethers (for examplediethyl ether, tetrahydrofuran, dioxane, etc.), nitriles (acetonitrile,benzonitrile, etc.), aprotic dipolar solvents (dimethylformamide,dimethylacetamide, hexamethylphosphoramide, dimethylsulfoxide,sulfolane, N-methylpyrrolidone, etc.).

The intermediate products having general formulae (III), (V), (VII),(VIII), (IX), (XII) and (XV) when not known per se, are easily preparedaccording to known methods of organic chemistry.

In some cases, the compounds having general formula (I), can be obtainedas two or more optical or geometric or position isomers.

It is therefore within the spirit of the present invention to considerboth the isomerically pure compounds having general formula (I), andmixtures of the same, optionally obtained during the preparation of thecompounds having general formula (I) or deriving from an incompleteseparation of the isomers, in any proportion.

As already mentioned, the compounds having general formula (I) have ahigh herbicidal activity which makes them suitable for use in theagricultural field for the defence of useful crops from weeds.

In particular the compounds object of the present invention areeffective in the control, in both preemergence and post-emergence, ofnumerous monocotyledonous and dicotyledonous weeds. At the same timethese compounds can show compatibility or absence of toxic effects withrespect to useful crops in pre- and/or post-emergence treatment.

The compounds of the present invention can act as total or selectiveherbicides also in relation to the amount of the active principle used.

Examples of weeds which can be efficaciously controlled by using thecompounds having general formula (I), are: Abutilon theofrasti, Alismaplantago, Amaranthus spp., Amni maius, Capsella bursa pastoris,Chenopodium album, Convolvulus sepium, Galium aparine, Geraniumdissectum, Ipomea spp., Matricaria spp., Papaver rhoaes, Phaseolusaureus, Polygonum persicaria, Portulaca oleracea, Sida spinosa, Sinapsisarvensis, Solanum nigrum, Stellaria media, Veronica spp., Viola spp.,Xanthium spp., Alopecurus myosuroides, Avena fatua, Cyperus spp.,Digitaria sanguinalis, Echinocloa spp., Heleocaris avicularis,Heteranthera spp., Panicum spp., Poa spp., Scirpus spp., Sorghum spp.,etc.

Many of the above compounds do not have toxic effects, at the dosage ofuse in agrarian applications, against one or more important crops, suchas rice (Oryza sativa), wheat (Triticum sp.), barley (Hordeum vulgare),corn (Zea mays), soya-bean (Glycine max).

A further object of the present invention relates to a method for thecontrol of weeds in cultivated areas by the application of the compoundshaving general formula (I).

The quantity of compound to be used for obtaining the desired effect canvary in relation to several factors, such as, for example, the compoundused, the crop to be preserved, the weed to be fought, the degree ofinfestation, the climatic conditions, the characteristics of the soil,the application method, etc.

Dosages of compound ranging from 1 g to 1000 g per hectare generallyprovide a sufficient control.

For use in agriculture, it is often advantageous to use compositionswith a herbicidal activity, containing, as active substance, one or morecompounds having general formula (I), possibly also as a mixture ofisomers.

Compositions can be used in the form of dry powders, wet powders,emulsifiable concentrated products, microemulsions, pastes, granulates,solutions, suspensions, etc.: the selection of the type of compositiondepends on the specific use.

The compositions are prepared according to known methods, for example bydiluting or dissolving the active ingredient with a solvent mediumand/or solid diluent, possibly in the presence of surface-active agents.

Kaolin, alumina, silica, talc, bentonite, chalk, quartz, dolomite,attapulgite, montmorillonite, diatom earth, cellulose, starch, etc, canbe used as inert solid diluents, or carriers.

Water, or organic solvents such as aromatic hydrocarbons (xylols,mixtures or alkyl benzenes, etc.), aliphatic hydrocarbons (hexane,cyclohexane, etc.), halogenated aromatic hydrocarbons (chlorobenzene,etc.), alcohols (methanol, propanol, butanol, octanol, etc.), esters(isobutyl acetate, etc.), ketones (acetone, cyclohexanone, acetophenone,isophorone, ethyl amyl ketone, etc.), or vegetal or mineral oils ormixture thereof, etc. can be used as inert liquid diluents.

Surface-active agents which can be used are wetting and emulsifyingagents of the non-ionic type (polyethoxylated alkyl phenols,polyethoxylated fatty alcohols, etc.), of the anionic type (alkylbenzene sulfonates, alkyl sulfonates, etc.), of the cationic type(quaternary salts of alkyl ammonium, etc.).

Dispersants can also be added (for example lignin and its salts,cellulose derivatives, alginates, etc.), stabilizers (for exampleantioxidants, UV absorbers, etc.).

In order to widen the range of activity of the above compositions, it ispossible to add other active ingredients, such as, for example, otherherbicides, fungicides, insecticides, acaricides, fertilizers, etc.

Examples of other herbicides which can be added to the compositionscontaining one or more compounds having general formula (I) are thefollowing:

-   acetochlor, acifluorfen, aclonifen, AKH-7088, alachlor, alloxydim,    ametryn, amicarbazone, amidosulfuron, amitrole, anilofos, asulam,    atrazine, azafenidin, azimsulfuron, aziprotryne, BAY MKH 6561,    beflubutamid, benazolin, benfluralin, benfuresate, bensulfuron,    bensulide, bentazone, benzfendizone, benzobicyclon, benzofenap,    benzthiazuron, bifenox, bilanafos, bispyribac-sodium, bromacil,    bromobutide, bromofenoxim, bromoxynil, butachlor, butafenacil,    butamifos, butenachlor, butralin, butroxydim, butylate, cafenstrole,    carbetamide, carfentrazone-ethyl, chlomethoxyfen, chloramben,    chlorbromuron, chlorbufam, chlorflurenol, chloridazon, chlorimuron,    chlornitrofen, chlorotoluron, chloroxuron, chlorpropham,    chlorsulfuron, chlorthal, chlorthiamid, cinidon ethyl, cinmethylin,    cinosulfuron, clethodim, clodinafop, clomazone, clomeprop,    clopyralid, cloransulam-methyl, cumyluron (JC-940), cyanazine,    cycloate, cyclosulfamuron, cycloxydim, cyhalofop-butyl, 2,4-D,    2,4-DB, daimuron, dalapon, desmedipham, desmetryn, dicamba,    dichlobenil, dichlorprop, dichlorprop-P, diclofop, diclosulam,    diethatyl, difenoxuron, difenzoquat, diflufenican, diflufenzopyr,    dimefuron, dimepiperate, dimethachlor, dimethametryn, dimethenamid,    dinitramine, dinoseb, dinoseb acetate, dinoterb, diphenamid,    dipropetryn, diquat, dithiopyr, 1-diuron, eglinazine, endothal,    EPTC, esprocarb, ethalfluralin, ethametsulfuron-methyl, ethidimuron,    ethiozin (SMY 1500), ethofumesate, ethoxyfen-ethyl (HC-252),    ethoxysulfuron, etobenzanid (HW 52), fenoxaprop, fenoxaprop-P,    fentrazamide, fenuron, flamprop, flamprop-M, flazasulfuron,    florasulam, fluazifop, fluazifop-P, fluazolate (JV 485),    flucarbazone-sodium, fluchloralin, flufenacet, flufenpyr ethyl,    flumetsulam, flumiclorac-pentyl, flumioxazin, flumipropin,    fluometuron, fluoroglycofen, fluoronitrofen, flupoxam, flupropanate,    flupyrsulfuron, flurenol, fluridone, flurochloridone, fluroxypyr,    flurtamone, fluthiacet-methyl, fomesafen, foramsulfuron, fosamine,    furyloxyfen, glufosinate, glyphosate, halosulfuron-methyl,    haloxyfop, haloxyfop-P-methyl, hexazinone, imazamethabenz, imazamox,    imazapic, imazapyr, imazaquin, imazethapyr, imazosulfuron,    indanofan, iodosulfuron, ioxynil, isopropalin, isoproturon, isouron,    isoxaben, isoxachlortole, isoxaflutole, isoxapyrifop, KPP-421,    lactofen, lenacil, linuron, LS830556, MCPA, MCPA-thioethyl, MCPB,    mecoprop, mecoprop-P, mefenacet, mesosulfuron, mesotrione,    metamitron, metazachlor, methabenzthiazuron, methazole,    methoprotryne, methyldymron, metobenzuron, metobromuron,    metolachlor, S-metolachlor, metosulam, metoxuron, metribuzin,    metsulfuron, molinate, monalide, monolinuron, naproanilide,    napropamide, naptalam, NC-330, neburon, nicosulfuron, nipyraclofen,    norflurazon, orbencarb, oryzalin, oxadiargyl, oxadiazon,    oxasulfuron, oxaziclomefone, oxyfluorfen, paraquat, pebulate,    pendimethalin, penoxsulam, pentanochlor, pentoxazone, pethoxamid,    phenmedipham, picloram, picolinafen, piperophos, prethylachlor,    primisulfuron, prodiamine, profluazol, proglinazine, prometon,    prometryne, propachlor, propanil, propaquizafop, propazine, propham,    propisochlor, propyzamide, prosulfocarb, prosulfuron, pyraclonil,    pyraflufenethyl, pyrazogyl (HSA-961), pyrazolynate, pyrazosulfuron,    pyrazoxyfen, pyribenzoxim, pyributicarb, pyridafol, pyridate,    pyriftalid, pyriminobac-methyl, pyrithiobac-sodium, quinclorac,    quinmerac, quizalofop, quizalofop-P, rimsulfuron, sethoxydim,    siduron, simazine, simetryn, sulcotrione, sulfentrazone,    sulfometuron-methyl, sulfosulfuron, 2,3,6-TBA, TCA-sodium, tebutam,    tebuthiuron, tepraloxydim, terbacil, terbumeton, terbuthyl-azine,    terbutryn, thenylchlor, thiazafluron, thiazopyr, thidiazimin,    thifensulfuron-methyl, thiobencarb, tiocarbazil, tioclorim,    tralkoxydim, tri-allate, triasulfuron, triaziflam, tribenuron,    triclopyr, trietazine, trifloxysulfuron, trifluralin,    triflusulfuron-methyl, tritosulfuron, UBI-C4874, vernolate.

The concentration of active substance in the above compositions can varywithin a wide range, depending on the active substance, the applicationsto which it is destined, the environmental conditions and type offormulation used. In general, the concentration of active substancepreferably ranges from 1 to 90%.

Some illustrative and non-limiting examples of the present invention areprovided hereunder.

Example 1 Preparation of methyl(2E)-4-(2-chloro-4-fluoro-5-isocyanatophenoxy)-3-methoxybut-2-enoate(Intermediate having formula II)

Trichloromethyl chloroformate (1.37 g) is added dropwise to a solutionof methyl(2E)-4-(5-amino-2-chloro-4-fluorophenoxy)-3-methoxybut-2-enoate (2.0 g)in ethyl acetate (30 ml). The mixture is stirred overnight at roomtemperature. It is concentrated under vacuum and the residue obtained(2.3 g) is used as such in the subsequent reaction.

Example 2 Preparation of methyl(2E)-4-{2-chloro-4-fluoro-5-[1,2,3,6-tetrahydro-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenoxy}-3-methoxybut-2-enoate(Compound No 1)

A solution of ethyl 3-amino-4,4,4-trifluoro-2-butenoate (1.39 g) indimethylformamide (5 ml) is added drop-wise to a suspension of sodiumhydride (60% in mineral oil) (0.3 g) in dimethylformamide (15 ml),cooled to 0° C. and kept in an inert atmosphere, the temperature beingmaintained below 5° C. At the end of the addition, the mixture isstirred for 1 hour at a temperature ranging from 2 to 4° C. A solutionof methyl(2E)-4-(2-chloro-4-fluoro-5-isocyanatophenoxy)-3-methoxybut-2-enoate(2.3 g), prepared in the previous example 1, in dimethylformamide (7 ml)is added dropwise to the solution thus obtained, maintaining thetemperature within the above-mentioned range.

The reaction mixture is subsequently heated to 80° C., maintained atthis temperature for 4.5 hours and finally stirred overnight at roomtemperature. The reaction mixture is poured into water (100 ml) andwashed with ethyl acetate (3×30 ml). The organic phase is extracted withwater that is added to the previous aqueous phase and acidified with 10%hydrochloric acid at a temperature of 5° C. The product which separatesis extracted with ethyl acetate and dried under vacuum. 2.74 g ofproduct are obtained, which are used as such in the following reaction.

¹H-NMR (CDCl₃): δ a 3.67, 3.69 (2s, 6H, CO₂CH₃, OCH₃); 5.20 (bs, 1H,CHCO₂Me); 5.25 (m, 2H, OCH₂); 6.23 (s, 1H, CH uracil); 6.9 (d, 1H,aromatic); 7.3 (d, 1H, aromatic).

Example 3 Preparation of methyl(2E)-4-{2-chloro-4-fluoro-5-[1,2,3,6-tetrahydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenoxy}-3-methoxybut-2-enoate(Compound No 2)

Methyl iodide (0.4 g) is added to a mixture of methyl(2E)-4-{2-chloro-4-fluoro-5-[1,2,3,6-tetrahydro-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenoxy}-3-methoxybut-2-enoate(0.89 g), obtained in the previous example 2, and potassium carbonate(0.4 g) in acetone (15 ml). The reaction mixture is refluxed for 5hours. Water is added (100 ml) after evaporation of the solvent, and themixture is extracted ethyl acetate (2×50 ml); the organic phase is driedwith sodium sulphate and concentrated under vacuum. The residue ispurified by chromatography on a silica gel column, eluting withn-hexane/ethyl acetate 6:4. 0.5 g of product are obtained.

¹H-NMR (CDCl₃): δ a 3.53 (bs, 1H, NCH₃); 3.66, 3.67 (2s, 6H, CO₂CH₃,OCH₃); 5.18 (bs, 1H, CHCO₂Me); 5.23 (m, 2H, OCH₂); 6.33 (s, 1H, CHuracil); 6.9 (d, 1H, aromatic); 7.3 (d, 1H, aromatic).

Example 4 Alternative preparation of methyl(2E)-4-{2-chloro-4-fluoro-5-[1,2,3,6-tetrahydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenoxy}-3-methoxybut-2-enoate(Compound No 2)

A solution of ethyl 4,4,4-trifluoro-3-(methylamino)-2-butenoate (3.25 g)in dimethylformamide (10 ml) is added drop-wise to a suspension ofsodium hydride (60% in mineral oil) (0.65 g) in dimethylformamide (35ml), cooled to 0° C. and kept in an inert atmosphere, maintaining thetemperature below 5° C. At the end of the addition, the solution isstirred for an hour at a temperature ranging from 2 to 4° C. A solutionof methyl(2E)-4-(2-chloro-4-fluoro-5-isocyanatophenoxy)-3-methoxybut-2-enoate(5.0 g) in dimethyl formamide (10 ml) is added drop-wise to the solutionthus obtained, maintaining the temperature within the above-mentionedrange.

The reaction mixture is then heated to 100° C., maintained at thistemperature for 6 hours and finally stirred overnight at roomtemperature. The reaction mixture is poured into water (200 ml) andwashed with ethyl acetate (3×50 ml). The organic phase is extracted withwater that is added to the previous aqueous phase and acidified with 10%hydrochloric acid at a temperature of 5° C. The product which separatesis extracted with ethyl acetate and dried under vacuum. The residue ispurified by chromatography on a silica gel column, eluting withn-hexane/ethyl acetate 6:4. 2.1 g of product are obtained.

Example 5

The following compounds were prepared (identified by elemental analysis,¹H- and ¹⁹F-NMR), following the procedures described in the aboveexamples:

-   methyl    (2E)-4-{2,4-dichloro-5-[1,2,3,6-tetrahydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenoxy}-3-methoxybut-2-enoate    (Compound No 3), m.p. 116° C.;-   ethyl    (2E)-4-{2-chloro-4-fluoro-5-[1,2,3,6-tetrahydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenoxy}-3-ethoxybut-2-enoate    (Compound No 4);-   ethyl    (2E)-4-{2,4-dichloro-5-[1,2,3,6-tetrahydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenoxy}-3-ethoxybut-2-enoate    (Compound No 5);

Example 6 Preparation of 3-{5-[(5-tert-butyl-1,3,4-oxadiazol-2-yl)methoxy]-4-chloro-2-fluorophenyl}-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione(Compound No 6)

2-tert-butyl-5-(chloromethyl)-1,3,4-oxadiazole (0.22 g) is added to amixture of3-(4-chloro-2-fluoro-5-hydroxyphenyl)-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione(0.40 g) and potassium carbonate (0.25 g) in dimethylformamide (5 ml).The reaction mixture is heated to 60° C. for 5 hours.

At the end of the reaction, the mixture is poured into water (50 ml) andextracted with ethyl acetate (2×30 ml); the organic phase is washed withwater, dried with sodium sulphate and concentrated under vacuum. Theresidue is purified by chromatography on a silica gel column, elutingwith n-hexane/ethyl acetate 8:2. 0.24 g of product are obtained as acolourless oil.

¹H-NMR (CDCl₃): δ a 1.41 (s, 9H, C(CH₃)₃); 3.53 (bs, 3H, NCH₃); 5.25 (s,2H, OCH₂); 6.33 (s, 1H, CH uracil); 7.1 (d, 1H, aromatic); 7.3 (d, 1H,aromatic).

Example 7

The following compounds (identified by elemental analysis, ¹H- and¹⁹F-NMR) were prepared following the procedure described in example 6:

-   3-[4-chloro-2-fluoro-5-(tetrazol-5-ylmethoxy)phenyl]-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione    (Compound No 7) m.p. 82° C.;-   3-{4-chloro-2-fluoro-5-[(2-ethyl-2H-tetrazol-5-yl)methoxy]phenyl}-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione    (Compound No 8) m.p. 126° C.;-   3-{4-chloro-2-fluoro-5-[(1-ethyl-1H-tetrazol-5-yl)methoxy]phenyl}-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione    (Compound No 9) m.p. 60° C.;-   methyl    [5-({2-chloro-4-fluoro-5-[1,2,3,6-tetrahydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenoxy}methyl)-1H-tetrazol-1-yl]acetate    (Compound No 10) m.p. 243° C.;-   methyl    [5-({2-chloro-4-fluoro-5-[1,2,3,6-tetrahydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenoxy}methyl)-2H-tetrazol-2-yl]acetate    (Compound No 11) m.p. 65° C.;

Example 8 Preparation of ethyl 4-chloro-3-cyanophenylcarbamate(Intermediate having formula X)

A solution of ethyl chloroformate (3.68 g) in methylene chloride (5 ml)is added dropwise in about 20 minutes to a mixture of5-amino-2-chlorobenzonitrile (5.2 g) and pyridine (2.77 g) in methylenechloride (75 ml), cooled to 0° C. and maintained in an inert atmosphere.At the end of the addition, the solution is stirred for 1 hour at 0° C.and is then brought to room temperature. At the end of the reaction, themixture is poured into water (100 ml) and extracted with methylenechloride (2×80 ml); the organic phase is washed with water (2×80 ml),dried with sodium sulphate and concentrated under vacuum. 7.2 g ofproduct are obtained.

¹H-NMR (CDCl₃): δ a 1.31 (t, 3H, CH₃); 4.24 (q, 2H, CH₂); 6.72 (bs, 1H,NH); 7.25-7.82 (m, 3H, aromatic).

Example 9 Preparation of2-chloro-5-[1,2,3,6-tetrahydro-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]benzonitrile

A solution of ethyl 3-amino-4,4,4-trifluoro-2-butenoate (3.48 g) indimethylformamide (7 ml) is added dropwise to a suspension of sodiumhydride (60% in mineral oil) (0.9 g) in dimethylformamide (20 ml),cooled to 0° C. and kept in an inert atmosphere, maintaining thetemperature below 5° C. At the end of the addition, the solution isstirred for 1 hour at a temperature between 0 and 5° C. A solution ofethyl 4-chloro-3-cyanophenylcarbamate (4.0 g), prepared in the previousexample 8, in dimethylformamide (30 ml) is added dropwise to thesolution thus obtained, the temperature being maintained within theabove-mentioned range.

The reaction mixture is then heated to 140° C. and maintained at thistemperature for 4.5 hours. It is subsequently poured into water (100ml), basified with 10% NaOH and extracted with ethyl ether (3×50 ml).The aqueous phase is acidified with 10% hydrochloric acid. The productwhich separates is extracted with ethyl acetate (2×80 ml) dried withsodium sulphate and concentrated under vacuum. 6.1 g of product areobtained, which is used as such in the subsequent reaction.

Example 10 Preparation of2-chloro-5-[1,2,3,6-tetrahydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]benzonitrile

Methyl iodide (10.8 g) is added to a mixture of2-chloro-5-[1,2,3,6-tetrahydro-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]benzonitrile(6.0 g), obtained in the previous example 9, and sodium bicarbonate(3.19 g) in acetone (70 ml). The reaction mixture is refluxed for 18hours. Water is added (200 ml) after the evaporation of the solvent, andthe mixture is extracted with ethyl acetate (3×100 ml), the organicphase is dried with sodium sulphate and concentrated under vacuum. Theresidue is purified by chromatography on a silica gel column by elutingwith n-hexane/ethyl acetate 4:6. 1.9 g of product are obtained.

¹H-NMR (CDCl₃): δ a 3.55 (bs, 3H, NCH₃); 6.38 (s, 1H, CH uracil);7.4-7.7 (m, 3H, aromatic).

Example 11 Preparation of3-[4-chloro-3-(tetrazol-5-yl)phenyl]-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione(Compound No 12)

Trimethylsilyl azide (1.34 g) and dibutyltin oxide (0.3 g) are added toa suspension of2-chloro-5-[1,2,3,6-tetrahydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]benzonitrile(1.9 g) in toluene (15 ml).

The reaction mixture is refluxed for 8 hours. After evaporation of thesolvent, the residue is treated with methanol (30 ml) and concentratedin vacuo. The raw product obtained (2.3 g) is purified by digestion withn-hexane (30 ml) at room temperature for 1 hour. 2.1 g of product areobtained having a melting point >180° C. (dec.).

¹H-NMR (CDCl₃): δ a 3.51 (bs, 3H, NCH₃); 6.39 (s, 1H, CH uracil);7.5-8.0 (m, 3H, aromatic).

¹⁹F-NMR (CDCl₃): δ a −64, 1 (s, 3F, CF₃).

Example 12 Preparation of3-[4-chloro-3-(2-methyl-2H-tetrazol-5-yl)phenyl]-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione(Compound No 13) and3-[4-chloro-3-(1-methyl-1H-tetrazol-5-yl)phenyl]-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione (Compound No 14)

Methyl iodide (1.22 g) is added to a mixture of3-[4-chloro-3-(tetrazol-5-yl)phenyl]-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione(1.6 g), obtained in the previous example 10, and potassium carbonate(0.89 g) in acetone (30 ml). The reaction mixture is refluxed for 2hours. After the evaporation of the solvent, water is added (100 ml) andthe mixture is extracted with ethyl acetate (2×50 ml); the organic phaseis dried with sodium sulphate and concentrated under vacuum. The residueis purified by chromatography on a silica gel column by eluting withn-hexane/ethyl acetate 4:6. The following compounds are obtained: 0.55 gof3-[4-chloro-3-(2-methyl-2H-tetrazol-5-yl)phenyl]-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedionehaving a melting point of 192° C.

¹H-NMR (CDCl₃): δ a 3.54 (bs, 3H, NCH₃ uracil); 4.42 (bs, 3H, NCH₃tetrazole); 6.36 (s, 1H, CH uracil); 7.23-7.94 (m, 3H, aromatic);

and 0.3 g of3-[4-chloro-3-(1-methyl-1H-tetrazol-5-yl)phenyl]-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedionehaving a melting point of 185° C.

¹H-NMR (CDCl₃): δ a 3.54 (bs, 3H, NCH₃ uracil); 4.04 (bs, 3H, NCH₃tetrazole); 6.36 (s, 1H, CH uracil); 7.2-7.7 (m, 3H, aromatic).

The assignment of the structures was effected on the basis of the NMRspectra.

Example 13

The following compounds (identified by elemental analysis, ¹H- and¹⁹F-NMR) were prepared, following the procedure described in example 12:

-   3-[4-chloro-3-(2-ethyl-2H-tetrazol-5-yl)phenyl]-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione    (Compound No 15) m.p. 136° C.;-   3-[4-chloro-3-(1-ethyl-1H-tetrazol-5-yl)phenyl]-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione    (Compound No 16) m.p. 202° C.;-   methyl    (5-{2-chloro-5-[1,2,3,6-tetrahydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenyl}-2H-tetrazol-2-yl)acetate    (Compound No 17) m.p. 172° C.;-   methyl    (5-{2-chloro-5-[1,2,3,6-tetrahydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenyl}-1H-tetrazol-1-yl)acetate    (Compound No 18) m.p. 130° C.

Example 14 Preparation ofN-[4-chloro-3-(4,5-dimethyl-1,3-thiazol-2-yl)phenyl]-4,4,4-trifluoro-3-oxobutaneamide

Ethyl trifluoroacetoacetate (2.54 g) is added to a solution of2-(5-amino-2-chlorophenyl)-4,5-dimethyl-1,3-thiazole (2.20 g) in 110 mlof toluene; a catalytic amount of 4-dimethylaminopyridine is added, thenthe mixture is heated to 110° C. while distilling off the solvent. Whenreaction is complete, the residue is concentrated under vacuum; 3.80 gof product are obtained.

Example 15 Preparation of3-amino-N-[4-chloro-3-(4,5-dimethyl-1,3-thiazol-2-yl)phenyl]-4,4,4-trifluorobut-2-eneamide

A mixture ofN-[4-chloro-3-(4,5-dimethyl-1,3-thiazol-2-yl)phenyl]-4,4,4-trifluoro-3-oxobutaneamide(3.80 g) and ammonium acetate (6.22 g) in 35 ml of ethyl acetate isrefluxed for 7 hours, then cooled to room temperature and diluted withethyl acetate (70 ml). The mixture is washed once with water and oncewith brine, then dried over sodium sulphate and concentrated undervacuum.

The residue is purified by chromatography on a silica gel column byeluting with n-hexane/ethyl acetate 9:1; 1.70 g of product are obtained.

Example 16 Preparation of3-[4-chloro-3-(4,5-dimethyl-1,3-thiazol-2-yl)phenyl]-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione(Compound No 19)

A solution of3-amino-N-[4-chloro-3-(4,5-dimethyl-1,3-thiazol-2-yl)phenyl]-4,4,4-trifluorobut-2-eneamide(1.70 g), pyridine (0.89 g) and a catalytic amount of4-dimethylaminopyridine in 61 ml of toluene is heated at 40° C., then asolution of diphosgene (2.24 g) in 4 ml of toluene is added dropwise.

The mixture is kept at 40° C. for 2 hours, then poured into water (100ml) and extracted with ethyl acetate (3×50 ml); the combined organicphases are washed once with water and once with brine, then dried oversodium sulphate and concentrated under vacuum. 2.00 g of product areobtained.

Example 17 Preparation of3-[4-chloro-3-(4,5-dimethyl-1,3-thiazol-2-yl)phenyl]-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione(Compound No 20)

Methyl iodide (0.84 g) is added to a mixture of3-[4-chloro-3-(4,5-dimethyl-1,3-thiazol-2-yl)phenyl]-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione(0.40 g), obtained in the previous example 16, and sodium bicarbonate(0.17 g) in acetone (5 ml). The reaction mixture is refluxed for 2hours. Water is added (20 ml) after the evaporation of the solvent, andthe mixture is extracted with ethyl acetate (3×20 ml); the organic phaseis dried with sodium sulphate and concentrated under vacuum. The residueis purified by chromatography on a silica gel column by eluting withn-hexane/ethyl acetate 8:2. 0.21 g of product are obtained, having amelting point of 200° C.

¹H-NMR (CDCl₃): δ 2.36 (s, 3H, thiazole-CH₃), 2.416 (s, 3H,thiazole-CH₃), 3.54 (bs, 1H, NCH₃); 6.36 (s, 1H, CH uracil); 7.13 (dd,1H, aromatic); 7.58 (d, 1H, aromatic), 8.18 (d, 1H, aromatic).

Example 18

The following compounds (identified by ¹H- and ¹⁹F-NMR elementalanalysis) were prepared following suitable procedures, some of which aredescribed in the previous examples:

-   methyl    (2E)-4-{2-chloro-4-fluoro-5-[1,2,3,6-tetrahydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenylthio}-3-methoxybut-2-enoate    (Compound No 21);-   methyl    (2E)-4-{2,4-dichloro-5-[1,2,3,6-tetrahydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenylthio}-3-methoxybut-2-enoate    (Compound No 22);-   isopropyl    (2E)-4-{2-chloro-4-fluoro-5-[1,2,3,6-tetrahydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenoxy}-3-methoxybut-2-enoate    (Compound N° 23);-   methyl    (2E)-4-{2,4-dichloro-5-[1,2,3,6-tetrahydro-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenoxy}-3-methoxybut-2-enoate    (Compound No 24);-   ethyl    (2E)-4-{2-chloro-4-fluoro-5-[1,2,3,6-tetrahydro-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenoxy}-3-ethoxybut-2-enoate    (Compound No 25);-   ethyl    (2E)-4-{2,4-dichloro-5-[1,2,3,6-tetrahydro-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenoxy}-3-ethoxybut-2-enoate    (Compound No 26);-   2,2,2-trifluoroethyl    (2E)-4-{2-chloro-4-fluoro-5-[1,2,3,6-tetrahydro-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenoxy}-3-methoxybut-2-enoate    (Compound No 27);-   (2E)-4-{2-chloro-4-fluoro-5-[1,2,3,6-tetrahydro-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenoxy}-3-methoxy-N,N-dimethylbut-2-enamide    (Compound No 28);-   S-ethyl    (2E)-4-{2-chloro-4-fluoro-5-[1,2,3,6-tetrahydro-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenoxy}-3-methoxybut-2-enethioate    (Compound No 29);-   isopropyl    (2E)-4-{2,4-dichloro-5-[1,2,3,6-tetrahydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenoxy}-3-methoxybut-2-enoate    (Compound No 30);-   2,2,2-trifluoroethyl    (2E)-4-{2-chloro-4-fluoro-5-[1,2,3,6-tetrahydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenoxy}-3-methoxybut-2-enoate    (Compound No 31);-   2,2,2-trifluoroethyl    (2E)-4-[2,4-dichloro-5-[(1,2,3,6-tetrahydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenoxy]-3-methoxybut-2-enoate    (Compound No 32);-   S-ethyl    (2E)-4-{2-chloro-4-fluoro-5-[1,2,3,6-tetrahydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)    pyrimidin-1-yl]phenoxy}-3-methoxybut-2-enethioate (Compound No 33);-   S-ethyl    (2E)-4-{2,4-dichloro-5-[1,2,3,6-tetrahydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenoxy}-3-methoxybut-2-enethioate    (Compound No 34);-   (2E)-4-{(2-chloro-4-fluoro-5-[1,2,3,6-tetrahydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenoxy}-3-methoxy-N,N-dimethylbut-2-enamide    (Compound No 35);-   (2E)-4-{2,4-dichloro-5-[1,2,3,6-tetrahydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenoxy}-3-methoxy-N,N-dimethylbut-2-enamide    (Compound No 36);-   (2E)-4-{2-chloro-4-fluoro-5-[1,2,3,6-tetrahydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenylthio}-3-methoxy-N,N-dimethylbut-2-enamide    (Compound No 37);-   (2E)-4-{2,4-dichloro-5-[1,2,3,6-tetrahydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenylthio}-3-methoxy-N,N-dimethylbut-2-enamide    (Compound No 38);-   3-[4-chloro-2-fluoro-5-(tetrazol-5-ylmethoxy)phenyl]-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione    (Compound No 39);-   3-{4-chloro-2-fluoro-5-[(2-methyl-2H-tetrazol-5-yl)methoxy]phenyl}-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione    (Compound No 40);-   3-[2,4-dichloro-5-(tetrazol-5-ylmethoxy)phenyl]-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione    (Compound No 41);-   3-{4-chloro-2-fluoro-5-[(2-methyl-2H-tetrazol-5-yl)    methoxy]phenyl}-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione    (Compound No 42), m.p. 167° C.;-   3-{2,4-dichloro-5-[(2-methyl-2H-tetrazol-5-yl)methoxy]phenyl}-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione    (Compound No 43);-   3-{2,4-dichloro-5-[(2-ethyl-2H-tetrazol-5-yl)methoxy]phenyl}-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione    (Compound No 44);-   3-{2,4-dichloro-5-[(1-ethyl-1H-tetrazol-5-yl)methoxy]phenyl}-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione    (Compound No 45);-   methyl    [5-({2,4-dichloro-5-[1,2,3,6-tetrahydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenoxy}methyl)-1H-tetrazol-1-yl]acetate    (Compound No 46);-   methyl    [5-({2,4-dichloro-5-[1,2,3,6-tetrahydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenoxy}methyl)-2H-tetrazol-2-yl]acetate    (Compound No 47);-   3-[4-chloro-3-(tetrazol-5-yl)phenyl]-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione    (Compound No 48);-   3-[4-chloro-3-(2-methyl-2H-tetrazol-5-yl)phenyl]-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione    (Compound No 49);-   3-[4-chloro-3-(1-methyl-1H-tetrazol-5-yl)phenyl]-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione    (Compound No 50);-   3-[4-chloro-2-fluoro-5-(tetrazol-5-yl)phenyl]-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione    (Compound No 51);-   3-[2,4-dichloro-5-(tetrazol-5-yl)phenyl]-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione    (Compound No 52);-   3-[4-chloro-2-fluoro-5-(tetrazol-5-yl)phenyl]-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione    (Compound No 53);-   3-[2,4-dichloro-5-(tetrazol-5-yl)phenyl]-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione    (Compound No 54);-   3-[4-chloro-2-fluoro-5-(2-methyl-2H-tetrazol-5-yl)phenyl]-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione    (Compound No 55);-   3-[2,4-dichloro-5-(2-methyl-2H-tetrazol-5-yl)phenyl]-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione    (Compound No 56);-   3-[4-chloro-2-fluoro-5-(1-methyl-1H-tetrazol-5-yl)phenyl]-6-(trifluoromethyl)-2,4(1H,3H)    pyrimidinedione (Compound No 57);-   3-[2,4-dichloro-5-(1-methyl-1H-tetrazol-5-yl)phenyl]-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione    (Compound No 58);-   3-[(4-chloro-2-fluoro-5-(2-methyl-2H-tetrazol-5-yl)phenyl]-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione    (Compound No 59);-   3-[2,4-dichloro-5-(2-methyl-2H-tetrazol-5-yl)phenyl]-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione    (Compound No 60);-   3-[4-chloro-2-fluoro-5-(1-methyl-1H-tetrazol-5-yl)phenyl]-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione    (Compound No 61);-   3-[2,4-dichloro-5-(1-methyl-1H-tetrazol-5-yl)phenyl]-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione    (Compound No 62);-   methyl    (5-{2-chloro-4-fluoro-5-[1,2,3,6-tetrahydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenyl}-1H-tetrazol-1-yl)    acetate (Compound No 63);-   methyl    (5-{2-chloro-4-fluoro-5-[(1,2,3,6-tetrahydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenyl}-2H-tetrazol-2-yl)acetate    (Compound No 64);-   methyl    (5-{2,4-dichloro-5-[1,2,3,6-tetrahydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenyl}-1H-tetrazol-1-yl)acetate    (Compound No 65);-   methyl    (5-{2,4-dichloro-5-[1,2,3,6-tetrahydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenyl}-2H-tetrazol-2-yl)acetate    (Compound No 66);-   3-[4-chloro-3-(4-methoxy-5-methyl-1,3-thiazol-2-yl)phenyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione    (Compound No 67);-   3-[2,4-dichloro-5-(4-methoxy-5-methyl-1,3-thiazol-2-yl)phenyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione    (Compound No 68);-   3-[4-chloro-2-fluoro-5-(4-methoxy-5-methyl-1,3-thiazol-2-yl)phenyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione    (Compound No 69);-   3-[4-chloro-3-(4-methoxy-5-methyl-1,3-thiazol-2-yl)phenyl-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione    (Compound No 70), m.p. 201° C.;-   3-[4-chloro-3-(4-ethoxy-5-methyl-1,3-thiazol-2-yl)phenyl-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione    (Compound No 71);-   3-[2,4-dichloro-5-(4-methoxy-5-methyl-1,3-thiazol-2-yl)phenyl-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione    (Compound No 72);-   3-[2,4-dichloro-5-(4-ethoxy-5-methyl-1,3-thiazol-2-yl)phenyl-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione    (Compound No 73);-   3-[4-chloro-2-fluoro-5-(4-methoxy-5-methyl-1,3-thiazol-2-yl)phenyl-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione    (Compound No 74);-   3-[4-chloro-2-fluoro-5-(4-ethoxy-5-methyl-1,3-thiazol-2-yl)phenyl-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione    (Compound No 75);-   3-[4-chloro-3-(4-benzyloxy-5-methyl-1,3-thiazol-2-yl)phenyl-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione    (Compound No 76);-   3-[2,4-dichloro-5-(4-benzyloxy-5-methyl-1,3-thiazol-2-yl)phenyl-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione    (Compound No 77);-   3-[4-chloro-2-fluoro-5-(4-benzyloxy-5-methyl-1,3-thiazol-2-yl)phenyl-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione    (Compound No 78);-   3-(2,4-dichloro-5-{[5-(trifluoromethyl)-1,3,4-thiadiazol-2-yl]oxy}phenyl)-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione    (Compound No 79);-   3-(4-chloro-2-fluoro-5-{[5-(trifluoromethyl)-1,3,4-thiadiazol-2-yl]oxy}phenyl)-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione    (Compound No 80);-   3-(2,4-dichloro-5-{[5-(trifluoromethyl)-1,3,4-oxadiazol-2-yl]oxy}phenyl)-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione    (Compound No 81);-   3-(4-chloro-2-fluoro-5-{[5-(trifluoromethyl)-1,3,4-oxadiazol-2-yl]oxy}phenyl)-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione    (Compound No 82);-   3-(4-chloro-3-{[5-(trifluoromethyl)-1,3,4-thiadiazol-2-yl]oxy}phenyl)-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione    (Compound No 83);-   3-(2,4-dichloro-5-{[5-(trifluoromethyl)-1,3,4-thiadiazol-2-yl]oxy}phenyl)-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione    (Compound No 84), m.p. 90° C.;-   3-(4-chloro-2-fluoro-5-{[5-(trifluoromethyl)-1,3,4-thiadiazol-2-yl]oxy}phenyl)-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione    (Compound No 85), m.p. 4 g° C.;-   3-(4-chloro-3-{[5-methyl-1,3,4-thiadiazol-2-yl]oxy}phenyl)-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione    (Compound No 86);-   3-(2,4-dichloro-5-{[(5-methyl-1,3,4-thiadiazol-2-yl)oxy]phenyl}-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione    (Compound No 87);-   3-{4-chloro-2-fluoro-5-[(5-methyl-1,3,4-thiadiazol-2-yl)oxy}phenyl]-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione    (Compound No 88);-   3-(4-chloro-3-{[5-(trifluoromethyl)-1,3,4-oxadiazol-2-yl]oxy}phenyl)-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione    (Compound No 89);-   3-(2,4-dichloro-3-{[5-(trifluoromethyl)-1,3,4-oxadiazol-2-yl]oxy}phenyl)-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione    (Compound No 90);-   3-(4-chloro-2-fluoro-5-{[5-(trifluoromethyl)-1,3,4-oxadiazol-2-yl]oxy}phenyl)-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione    (Compound No 91);-   3-{4-chloro-3-[(5-methyl-1,3,4-oxadiazol-2-yl)oxy]phenyl}-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione    (Compound No 92);-   3-{2,4-dichloro-5-[(5-methyl-1,3,4-oxadiazol-2-yl)oxy]phenyl}-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione    (Compound No 93);-   3-{4-chloro-2-fluoro-5-[(5-methyl-1,3,4-oxadiazol-2-yl)oxy]phenyl}-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione    (Compound No 94);-   methyl    (2E)-4-{2-chloro-4-fluoro-5-[1,2,3,6-tetrahydro-3-methyl-6-oxo-2-thioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenoxy}-3-methoxybut-2-enoate    (Compound No 95);-   methyl    (2E)-4-{2-chloro-4-fluoro-5-[1,2,3,6-tetrahydro-3-difluoromethyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenoxy}-3-methoxybut-2-enoate    (Compound No 96).-   methyl    (2E)-4-{2,4-dichloro-5-[1,2,3,6-tetrahydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenoxy}-3-methoxypent-2-enoate    (Compound No 97);-   methyl    (2E)-4-{2-chloro-4-fluoro-5-[1,2,3,6-tetrahydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenoxy}-3-methoxypent-2-enoate    (Compound No 98);-   ethyl    (2E)-4-{2,4-dichloro-5-[1,2,3,6-tetrahydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenoxy}-3-methoxybut-2-enoate    (Compound No 99), m.p. 128° C.;-   ethyl    (2E)-4-{2-chloro-4-fluoro-5-[1,2,3,6-tetrahydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenoxy}-3-methoxybut-2-enoate    (Compound No 100), m.p. 78° C.;-   3-{4-chloro-3-[2-(methoxymethyl)-2H-tetrazol-5-yl]phenyl}-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione    (Compound No 101), m.p. 80° C.;-   3-{4-chloro-3-[1-(methoxymethyl)-1H-tetrazol-5-yl]phenyl}-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione    (Compound No 102), m.p. 182° C.;-   3-{4-chloro-3-[2-(ethoxymethyl)-2H-tetrazol-5-yl]phenyl}-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione    (Compound No 103), m.p. 140° C.;-   3-{4-chloro-3-[1-(ethoxymethyl)-1H-tetrazol-5-yl]phenyl}-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione    (Compound No 104), m.p. 157° C.;-   3-[3-(2-allyl-2H-tetrazol-5-yl)-4-chlorophenyl]-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione    (Compound No 105), m.p. 116° C.;-   3-[3-(1-allyl-1H-tetrazol-5-yl)-4-chlorophenyl]-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione    (Compound No 106), m.p. 160° C.;-   3-{4-chloro-2-fluoro-5-[(3-methylisoxazol-5-yl)methoxy]phenyl}-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione    (Compound No 107), m.p. 154° C.;-   3-{2,4-dichloro-5-[(3-methylisoxazol-5-yl)methoxy]phenyl}-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione    (Compound No 108), m.p. 185° C.;-   3-[4-chloro-3-(4-isopropoxy-5-methyl-1,3-thiazol-2-yl)phenyl-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione    (Compound No 109), m.p. 124° C.;-   3-[4-chloro-3-(4-hydroxy-5-methyl-1,3-thiazol-2-yl)phenyl-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione    (Compound No 110), m.p. 165° C.;-   3-{4-chloro-2-fluoro-5-[(5-methyl-1,2,4-oxadiazol-3-yl)methoxy]phenyl}-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione    (Compound No 111);-   3-{2,4-dichloro-5-[(5-methyl-1,2,4-oxadiazol-3-yl)methoxy]phenyl}-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione    (Compound No 112), m.p. 167° C.;-   3-[3-(1,3-benzothiazol-2-yl)-4-chlorophenyl]-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione    (Compound No 113), m.p. 189° C.;-   3-[3-(1,3-benzoxazol-2-yl)-4-chlorophenyl]-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione    (Compound No 114), m.p. 183° C.;-   3-{4-chloro-2-fluoro-5-[(3-methyl-1,2,4-oxadiazol-5-yl)methoxy]phenyl}-1-methyl-6-(trifluoromethyl)-2,4(1H,3N)-pyrimidinedione    (Compound No 115), m.p. 60° C.;-   3-[4-chloro-3-(4-methyl-1,3-thiazol-2-yl)phenyl-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione    (Compound No 116);-   3-[4-chloro-2-fluoro-5-(1,2,4-oxadiazol-3-ylmethoxy)phenyl]-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione    (Compound No 117), m.p. 122° C.;-   3-[3-(2-tert-butyl-2H-tetrazol-5-yl)-4-chlorophenyl]-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione    (Compound No 118), m.p. 154° C.;-   3-[5-(1,3-benzothiazol-2-yl)-4-chloro-2-fluorophenyl]-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione    (Compound No 119), m.p. 211° C.;-   3-(4-chloro-3-{2-[(2-methoxyethoxy)methyl]-2H-tetrazol-5-yl}phenyl)-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione    (Compound No 120);-   3-(4-chloro-3-{1-[(2-methoxyethoxy)methyl]-1H-tetrazol-5-yl}phenyl)-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione    (Compound No 121);-   3-[5-(1,3-benzoxazol-2-yl)-4-chloro-2-fluorophenyl]-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione    (Compound No 122), m.p. 178° C.;-   3-[5-(1,3-benzothiazol-2-yl)-2,4-dichlorophenyl]-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione    (Compound No 123), m.p. 195° C.;-   3-[2,4-dichloro-5-(6-methyl-1,3-benzoxazol-2-yl)phenyl]-1-methyl-6-(trifluoromethyl)    2,4(1H,3H)-pyrimidinedione (Compound No 124), m.p. 200° C.;-   2-(5-{2-chloro-5-[1,2,3,6-tetrahydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenyl}-2H-tetrazol-2-yl)-N,N-dimethylacetamide    (Compound No 125) m.p. 208° C.;-   2-(5-{2-chloro-5-[1,2,3,6-tetrahydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenyl}-2H-tetrazol-2-yl)acetamide    (Compound No 126) m.p. 200° C.;-   3-[2,4-dichloro-5-(4-methyl-1,3-thiazol-2-yl)phenyl-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione    (Compound No 127), m.p. 188° C.;-   3-[(3-(4-tert-butyl-1,3-thiazol-2-yl)-4-chlorophenyl]-1-methyl-6-(trifluoromethyl)    2,4(1H,3H)-pyrimidinedione (Compound No 128), m.p. 173° C.;-   3-[2,4-dichloro-5-(4-isobutyl-1,3-thiazol-2-yl)phenyl]-1-methyl-6-(trifluoromethyl)    2,4(1H,3H)-pyrimidinedione (Compound No 129), m.p. 167° C.;-   3-[4-chloro-3-(1,3-thiazol-2-yl)phenyl]-1-methyl-6-(trifluoromethyl)    2,4(1H,3H)-pyrimidinedione (Compound No 130);-   ethyl    2-{2-chloro-5-[1,2,3,6-tetrahydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenyl}-4-methyl-1,3-thiazole-5-carboxylate    (Compound No 131), m.p. 200° C.;-   3-{5-[(3-tert-butylisoxazol-5-yl)methoxy]-4-chloro-2-fluorophenyl}-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione    (Compound No 132), m.p. 142° C.;-   3-{4-chloro-2-fluoro-5-[(3-isopropylisoxazol-5-yl)methoxy]phenyl}-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione    (Compound No 133), m.p. 128° C.;-   3-[4-chloro-3-(2-isopropyl-2H-tetrazol-5-yl)phenyl]-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione    (Compound No 134) m.p. 147° C.;-   3-[3-(2-benzyl-2H-tetrazol-5-yl)-4-chlorophenyl]-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione    (Compound No 135);-   3-[3-(1-benzyl-1H-tetrazol-5-yl)-4-chlorophenyl]-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione    (Compound No 136);-   3-{4-chloro-2-fluoro-5-[(1-methyl-1H-tetrazol-5-yl)    oxy]phenyl}-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione    (Compound No 137);-   3-{4-chloro-2-fluoro-5-[(2-methyl-2H-tetrazol-5-yl)oxy]phenyl}-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione    (Compound No 138);-   methyl    (2E)-4-{2-chloro-5-[1,2,3,6-tetrahydro-3-methyl-2,6-dioxo-4(trifluoromethyl)pyrimidin-1-yl]phenoxy}-3-methoxybut-2-enoate    (Compound No 139);-   ethyl    (2E)-4-{(2-chloro-5-[1,2,3,6-tetrahydro-3-methyl-2,6-dioxo-4(trifluoromethyl)pyrimidin-1-yl]phenoxy}-3-ethoxybut-2-enoate    (Compound No 140);-   3-[4-chloro-3-(1,2,4-oxadiazol-3-ylmethoxy)phenyl]-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione    (Compound No 141);-   3-{4-chloro-3-[(3-methylisoxazol-5-yl)methoxy]phenyl}-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione    (Compound No 142);-   3-[4-chloro-3-(4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl)phenyl]-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione    (Compound No 143);-   3-[4-chloro-3-(5,6-dihydro-1,4,2-dioxazin-3-yl)phenyl]-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione    (Compound No 144);-   3-[4-chloro-3-(4-methyl-5-oxo-5,6-dihydro-4H-1,3,4-oxadiazin-2-yl)phenyl]-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione    (Compound No 145);-   3-[4-chloro-3-(5,6-dihydro-1,4,2-dioxazin-3-ylmethoxy)-2-fluorophenyl]-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione    (Compound No 146);-   3-{4-chloro-2-fluoro-5-[(4-methyl-5-oxo-5,6-dihydro-4H-1,3,4-oxadiazin-2-yl)methoxy]phenyl}-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimldinedione    (Compound No 147);-   3-[4-chloro-3-(2-phenyl-2H-tetrazol-5-yl)phenyl]-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione    (Compound No 148);-   3-[4-chloro-3-(1-phenyl-1H-tetrazol-5-yl)phenyl]-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione    (Compound No 149);-   3-{4-chloro-3-[1-(cyclopropylmethyl)-1H-tetrazol-5-yl]phenyl}-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione    (Compound No 150);-   3-{4-chloro-3-[2-(cyclopropylmethyl)-2H-tetrazol-5-yl]phenyl}-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione    (Compound No 151);-   3-{4-chloro-3-[1-(2-oxopropyl)-1H-tetrazol-5-yl]phenyl}-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione    (Compound No 152);-   3-{4-chloro-3-[2-(2-oxopropyl)-2H-tetrazol-5-yl]phenyl}-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione    (Compound No 153);-   3-[4-chloro-3-(4-cyclopropyl-1,3-thiazol-2-yl)phenyl]-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione    (Compound No 154);-   3-{4-chloro-3-[4-(4-chlorophenyl)-1,3-thiazol-2-yl]phenyl}-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione    (Compound No 155);-   ethyl    2-{2-chloro-5-[1,2,3,6-tetrahydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenyl}-1,3-thiazole-4-carboxylate    (Compound No 156), m.p. 197° C.;-   3-[3-(2-butyl-2H-tetrazol-5-yl)-4-chlorophenyl]-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione    (Compound No 157), m.p. 108° C.;-   3-[4-chloro-2-fluoro-5-(5,6-dihydro-1,4,2-dioxazin-3-ylmethoxy)-2-fluorophenyl]-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione    (Compound No 158);-   3-(4-chloro-3-{2-[(4-chlorophenoxy)methyl]-2H-tetrazol-5-yl}phenyl)-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione    (Compound No 159);-   3-(4-chloro-3-{1-[(4-chlorophenoxy)methyl]-1H-tetrazol-5-yl}phenyl)-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione    (Compound No 160);-   3-[3-(4-tert-butyl-5-oxo-4,5-dihydro-1,3,4-thiadiazol-2-yl)-4-chlorophenyl]-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione    (Compound No 161);-   3-{4-chloro-3-[2-(4-chlorobenzyl)-2H-tetrazol-5-yl]phenyl}-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione    (Compound No 162);-   3-{4-chloro-3-[1-(4-chlorobenzyl)-1H-tetrazol-5-yl]phenyl}-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione    (Compound No 163);-   methyl    2-{2-chloro-5-[1,2,3,6-tetrahydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenyl}-1,3-thiazole-4-carboxylate    (Compound No 164);-   methyl    (2-{2-chloro-5-[1,2,3,6-tetrahydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenyl}-1,3-thiazol-4-yl)acetate    (Compound No 165).

Example 19 Determination of the Herbicidal Activity and Phytotoxicity inPre-Emergence

The herbicidal activity of the compounds of the invention inpre-emergence was evaluated according to the following operativeprocedures.

The vegetable species of interest (weeds or crops) were sown in potswith an upper diameter of 10 cm, a height of 10 cm and containing sandysoil. 10 pots were used for each vegetable species.

Water was added to each pot in such a quantity as to germinate theseeds. The pots were divided into two groups, each containing 5 pots foreach weed or crop.

After one day from the sowing, the first set of pots was treated with ahydro-acetonic dispersion containing acetone at 10% in volume, theproduct under evaluation at the desired concentration and Tween 20 at0.5%.

The second set was treated with a hydro-acetonic solution only,containing acetone at 10% in volume and Tween 20 at 0.5%, and was usedas comparison (blank).

All pots were kept under observation in a conditioned environment underthe following conditions:

temperature: 24° C.;

relative humidity: 60%;

photoperiod: 16 ore;

light intensity: 10000 lux.

The pots were uniformly watered in order to ensure a sufficient humiditydegree for a good development of the plants.

Fifteen days after the treatment, the herbicidal activity was evaluatedon the basis of the following values, which refer to the damagepercentage tested on the treated plants, with respect to the non-treatedplants (blank):

0=0-10% damage;

1=11-30% damage;

2=31-50% damage;

3=51-70% damage;

4=71-90% damage;

5=91% damage—death of the plant.

Table 1 shows the results obtained by treating the vegetable specieslisted below with compounds 2, 6 and 13 with a dosage of 15 g/ha:

Abutilon theofrasti (AT); Amaranthus retroflexus (AR); Chenopodium album(CA); Convolvulus sepium (CS); Galium aparine (GA); Ipomea purpurea(IP); Portulaca oleracea (PO); Solanum nigrum (SN); Sida spinosa (SS).

TABLE 1 Herbicidal activity in pre-emergence with a dosage of 15 g/haVegetal species AT AR CA CS GA IP PO SN SS Compound No 2 5 5 5 5 5 5 5 55 Compound No 6 5 4 5 — 5 4 5 5 5 Compound No 13 5 5 5 — 5 5 5 5 5

Example 20 Determination of the Herbicidal Activity and Phytotoxicity inPost-Emergence

The herbicidal activity of the compounds of the invention inpost-emergence was evaluated according to the following operativeprocedures.

The vegetable species of interest (weeds or crops) were sown in potswith an upper diameter of 10 cm, a height of 10 cm and containing sandysoil. 10 pots were used for each vegetable species.

Water was added to each pot in such a quantity as to germinate theseeds. The pots were divided into two groups, each containing 5 pots foreach weed or crop.

Fifteen days after sowing (ten, in the case of wheat), when the weedsand crops, according to the species, were 10-15 cm high, the first setof pots was treated with a hydro-acetonic dispersion containing acetoneat 10% in volume, the product under evaluation at the desiredconcentration and Tween 20 at 0.5%.

The second set was treated with a hydro-acetonic solution only,containing acetone at 10% in volume and Tween 20 at 0.5%, and was usedas comparison (blank).

All pots were kept under observation in a conditioned environment underthe following conditions:

temperature: 24° C.;

relative humidity: 60%;

photo-period: 16 ore;

light intensity: 10000 lux.

The pots were uniformly watered every other day so as to ensure ahumidity degree sufficient for a good development of the plants.

The herbicidal activity was evaluated fifteen days after the treatment,on the basis of the following values which refer to the percentage ofdamage tested on the treated plants with respect to the non-treatedplants (blank):

0=0-10% damage;

1=11-30% damage;

2=31-50% damage;

3=51-70% damage;

4=71-90% damage;

5=91% damage—death of the plant.

Table 2 shows the results obtained by treating the vegetable specieslisted below with compounds 2, 6 and 13 with a dosage of 15 g/ha:

Abutilon theofrasti (AT); Amaranthus retroflexus (AR); Chenopodium album(CA); Convolvulus sepium (CS); Galium aparine (GA); Ipomea purpurea(IP); Portulaca oleracea (PO); Solanum nigrum (SN); Sida spinosa (SS).

TABLE 2 Herbicidal activity in post-emergence with a dosage of 15 g/haVegetable species AT AR CA CS GA IP PO SN SS Compound No 2 5 5 5 5 5 5 45 5 Compound No 6 5 3 4 — — 5 4 5 4 Compound No 13 5 5 5 — — 5 5 5 5

1. A compound having formula (I):

wherein: X₁ represents a hydrogen atom or a halogen atom; X₂ representsa halogen atom; X₄ represents a C₁-C₃ haloalkyl group; R represents ahydrogen atom, a C₁-C₃ alkyl group or a C₁-C₃ haloalkyl group; Grepresents an oxygen atom or a sulphur atom; X₃ represents aQ(CR₁R₂)_(n)Z— group, a Q₂- group, a Y (CO)—CR₆═CR₅—CR₃R₄Z— group; Zrepresents an oxygen atom or a sulphur atom; R₁, R₂, R₃ and R₄, the sameor different, represent a hydrogen atom or, a C₁-C₄ alkyl group; R₅represents an OR₇ group; R₆ represents a hydrogen atom or a C₁-C₄ alkylgroup; R₇ represents a C₁-C₄ alkyl group or a C₁-C₄ haloalkyl group; Yrepresents a C₄-C₆ alkoxy or haloalkoxy group; n represents 1, 2 or 3; Qrepresents a heterocyclic group selected from 1,3,4-oxadiazolyl,1,3,4-thiadiazolyl, 1,2,4-thiadiazolyl and 1,2,4-oxadiazolyl, saidgroups, in turn, being optionally substituted with a halogen atomselected from chlorine, fluorine, bromine or iodine, or with a groupselected from C₁-C₆ alkyl or C₁-C₆ haloalkyl, C₂-C₆ alkenyl or C₂-C₆haloalkenyl, C₂-C₆ alkynyl or C₂-C₆ haloalkynyl, Q₂ represents aheterocyclic group selected from 1H-tetrazol-5-yl or 2H-tetrazol-5-yl,being optionally substituted with a group selected from: C₁-C₆ alkyl;C₁-C₆ haloalkyl; C₂-C₆ alkenyl; C₂-C₆ haloalkenyl; C₂-C₆ alkynyl; C₂-C₆haloalkynyl, C₂-C₆ alkoxyalkyl; C₂-C₆ haloalkoxyalkyl; C₃-C₈alkoxyalkoxyalkyl, C₆-C₁₂ arylalkyl, C₇-C₁₂ aryloxyalkyl, C₈-C₁₂arylalkyloxyalkyl said groups in turn being optionally substituted withhalogen atoms, C₁-C₄ alkyl groups, C₁-C₃ haloalkyl groups, C₁-C₄ alkoxygroups, C₁-C₃ haloalkoxy groups, CN; C₃-C₇ cycloalkyl, C₆-C₁₂cycloalkylalkyl, tetrahydropyran-2-yl said groups in turn beingoptionally substituted with halogen atoms, C₁-C₄ alkyl groups, C₁-C₄alkoxy groups.
 2. A compound according to claim 1, characterized in thatit is selected from: methyl(2E)-4-{2-chloro-4-fluoro-5-[1,2,3,6-tetrahydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenoxy}-3-methoxybut-2-enoate;methyl(2E)-4-{2,4-dichloro-5-[1,2,3,6-tetrahydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenoxy}-3-methoxybut-2-enoate;methyl(2E)-4-{2-chloro-4-fluoro-5-[1,2,3,6-tetrahydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenylthio}-3-methoxybut-2-enoate;ethyl(2E)-4-{2-chloro-4-fluoro-5-[1,2,3,6-tetrehydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenoxy}-3-ethoxybut-2-enoate;methyl(2E)-4-{2,4-dichloro-5-[1,2,3,6-tetrahydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenylthio}-3-methoxybut-2-enoate;ethyl(2E)-4-{2,4-dichloro-5-[1,2,3,6-tetrahydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenoxy}-3-ethoxybut-2-enoate;isopropyl(2E)-4-{2-chloro-4-fluoro-5-[1,2,3,6-tetrahydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenoxy}-3-methoxybut-2-enoate;methyl(2E)-4-{2-chloro-4-fluoro-5-[1,2,3,6-tetrahydro-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenoxy}-3-methoxybut-2-enoate;methyl(2E)-4-{2,4-dichloro-5-[1,2,3,6-tetrahydro-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenoxy}-3-methoxybut-2-enoate;ethyl(2E)-4-{2-chloro-4-fluoro-5-[1,2,3,6-tetrahydro-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenoxy}-3-ethoxybut-2-enoate;isopropyl(2E)-4-{2,4-dichloro-5-[1,2,3,6-tetrahydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenoxy}-3-methoxybut-2-enoate;2,2,2-trifluoroethyl(2E)-4-{2-chloro-4-fluoro-5-[1,2,3,6-tetrahydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenoxy}-3-methoxybut-2-enoate;2,2,2-trifluoroethyl(2E)-4-{2,4-dichloro-5-[1,2,3,6-tetrahydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenoxy}-3-methoxybut-2-enoate;3-{5-[(5-tert-butyl-1,3,4-oxadiazol-2-yl)methoxy]-4-chloro-2-fluorophenyl}-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;3-[4-chloro-3-(tetrazol-5-yl)phenyl]-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;3-[4-chloro-3-(2-methyl-2H-tetrazol-5-yl)phenyl]-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;3-[4-chloro-3-(1-methyl-1H-tetrazol-5-yl)phenyl]-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;3-[4-chloro-3-(tetrazol-5-yl)phenyl]-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;3-[4-chloro-2-fluoro-5-(tetrazol-5-yl)phenyl]-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;3-[2,4-dichloro-5-(tetrazol-5-yl)phenyl]-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;3-[4-chloro-2-fluoro-5-(tetrazol-5-yl)phenyl]-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;3-[2,4-dichloro-5-(tetrazol-5-yl)phenyl]-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;3-[4-chloro-3-(2-methyl-2H-tetrazol-5-yl)phenyl]-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;3-[4-chloro-2-fluoro-5-(2-methyl-2H-tetrazol-5-yl)phenyl]-6-(trifluoromethyl)-2,4 (1H,3H)-pyrimidinedione;3-[2,4-dichloro-5-(2-methyl-2H-tetrazol-5-yl)phenyl]-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;3-[4-chloro-2-fluoro-5-(1-methyl-1H-tetrazol-5-yl)phenyl]-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;3-[2,4-dichloro-5-(1-methyl-1H-tetrazol-5-yl)phenyl]-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;3-[4-chloro-2-fluoro-5-(2-methyl-2H-tetrazol-5-yl)phenyl]-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;3-[2,4-dichloro-5-(2-methyl-2H-tetrazol-5-yl)phenyl]-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;3-[4-chloro-3-(2-ethyl-2H-tetrazol-5-yl)phenyl]-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;3-[4-chloro-3-(1-methyl-1H-tetrazol-5-yl)phenyl]-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;3-[4-chloro-2-fluoro-5-(1-methyl-1H-tetrazol-5-yl)phenyl]-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;3-[2,4-dichloro-5-(1-methyl-1H-tetrazol-5-yl)phenyl]-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;3-[4-chloro-3-(1-ethyl-1H-tetrazol-5-yl)phenyl]-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;methyl(2E)-4-{(2-chloro-4-fluoro-5-[1,2,3,6-tetrahydro-3-methyl-6-oxo-2-thioxo-4-(trifluoromethyl)pyrimidin-1-yl]-phenoxy}-3-methoxybut-2-enoate;methyl(2E)-4-{2-chloro-4-fluoro-5-[1,2,3,6-tetrahydro-3-difluoromethyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenoxy}-3-methoxybut-2-enoate;methyl(2E)-4-{2,4-dichloro-5-[1,2,3,6-tetrahydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenoxy}-3-methoxypent-2-enoate;methyl(2E)-4-{2-chloro-4-fluoro-5-[1,2,3,6-tetrahydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenoxy}-3-methoxypent-2-enoate;ethyl(2E)-4-{2,4-dichloro-5-[1,2,3,6-tetrahydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenoxy}-3-methoxybut-2-enoate;ethyl(2E)-4-{2-chloro-4-fluoro-5-[1,2,3,6-tetrahydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenoxy}-3-methoxybut-2-enoate;3-{4-chloro-3-[2-(methoxymethyl)-2H-tetrazol-5-yl]phenyl}-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;3-{4-chloro-3-[1-(methoxymethyl)-1H-tetrazol-5-yl]phenyl}-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;3-{4-chloro-3-[2-(ethoxymethyl)-2H-tetrazol-5-yl]phenyl}-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;3-{4-chloro-3-[1-(ethoxymethyl)-1H-tetrazol-5-yl]phenyl}-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;3-[3-(2-allyl-2H-tetrazol-5-yl)-4-chlorophenyl]-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;3-[3-(1-allyl-1H-tetrazol-5-yl)-4-chlorophenyl]-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;3-{4-chloro-2-fluoro-5-[(5-methyl-1,2,4-oxadiazol-3-yl)methoxy]phenyl}-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;3-{2,4-dichloro-5-[(5-methyl-1,2,4-oxadiazol-3-yl)methoxy]phenyl}-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;3-{4-chloro-2-fluoro-5-[(3-methyl-1,2,4-oxadiazol-5-yl)methoxy]phenyl}-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;3-[4-chloro-2-fluoro-5-(1,2,4-oxadiazol-3-ylmethoxy)phenyl]-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;3-[3-(2-tert-butyl-2H-tetrazol-5-yl)-4-chlorophenyl]-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;3-(4-chloro-3-{2-[(2-methoxyethoxy)methyl]-2H-tetrazol-5-yl}phenyl)-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;3-(4-chloro-3-{1-[(2-methoxyethoxy)methyl]-1H-tetrazol-5-yl}phenyl)-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;3-[4-chloro-3-(2-isopropyl-2H-tetrazol-5-yl)phenyl]-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;3-[3-(2-benzyl-2H-tetrazol-5-yl)-4-chlorophenyl]-1-methyl-6-(trifluoromethyl)-2,4(3H)-pyrimidinedione;3-[3-(1-benzyl-1H-tetrazol-5-yl)-4-chlorophenyl]-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;methyl (2E)-4-{2-chloro-5-[1,2,3,6-tetrahydro-3-methyl-2,6-dioxo-4(trifluoromethyl)pyrimidin-1-yl]phenoxy}-3-methoxybut-2-enoate; ethyl(2E)-4-{2-chloro-5-[1,2,3,6-tetrahydro-3-methyl-2,6-dioxo-4(trifluoromethyl) pyrimidin-1-yl]phenoxy}-3-ethoxybut-2-enoate;3-[4-chloro-3-(1,2,4-oxadiazol-3-ylmethoxy)phenyl]-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;3-{4-chloro-3-[1-(cyclopropylmethyl)-1H-tetrazol-5-yl]phenyl}-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;3-{4-chloro-3-[2-(cyclopropylmethyl)-2H-tetrazol-5-yl]phenyl}-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;3-[3-(2-butyl-2H-tetrazol-5-yl)-4-chlorophenyl]-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;3-(4-chloro-3-{2-[(4-chlorophenoxy)methyl]-2H-tetrazol-5-yl}phenyl)-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;3-(4-chloro-3-{1-[(4-chlorophenoxy)methyl]-1H-tetrazol-5-yl}phenyl)-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;3-{4-chloro-3-[2-(4-chlorobenzyl)-2H-tetrazol-5-yl]phenyl}-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;3-{4-chloro-3-[1-(4-chlorobenzyl)-1H-tetrazol-5-yl]phenyl}-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;methyl2-{2-chloro-5-[1,2,3,6-tetrahydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenyl}-1,3-thiazole-4-carboxylate;methyl(2-{2-chloro-5-[1,2,3,6-tetrahydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenyl}-1,3-thiazol-4-yl)acetate.3. A herbicidal composition containing, as active principle, aneffective amount of one or more compounds having formula (I) accordingto claim 1 and a non-phytotoxic carrier.
 4. The herbicidal compositionaccording to claim 3, characterized in that the concentration of theactive substance ranges from 1 to 90%.
 5. A compound as defined in claim1 wherein Q is 1,2,4-oxadiazolyl.
 6. A compound as defined in claim 1wherein Q is 5-methyl-1,2,4-oxadiazolyl.